A Strategy for the Convergent and Stereoselective Assembly of Polycyclic Molecules
The stereoselective oxidative coupling of cyclic ketones via silyl bis-enol ethers followed by ring-closing metathesis is shown to be a general and powerful reaction sequence for the preparation of diverse polycyclic scaffolds from simple precursors. The modular strategy successfully constructs subs...
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| Published in | Journal of the American Chemical Society Vol. 140; no. 5; pp. 1956 - 1965 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
07.02.2018
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0002-7863 1520-5126 1520-5126 |
| DOI | 10.1021/jacs.7b13234 |
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| Abstract | The stereoselective oxidative coupling of cyclic ketones via silyl bis-enol ethers followed by ring-closing metathesis is shown to be a general and powerful reaction sequence for the preparation of diverse polycyclic scaffolds from simple precursors. The modular strategy successfully constructs substructures prevalent in numerous bioactive natural product families, varying in substitution and carbocyclic composition. Several of the prepared compounds were shown to possess potent cytotoxic activity against a panel of tumor cell lines. The utility of this strategy was further demonstrated by a concise and highly convergent 17-step formal synthesis of the complex antimalarial marine diterpene, (+)-7,20-diisocyanoadociane. |
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| AbstractList | The stereoselective oxidative coupling of cyclic ketones via silyl bis-enol ethers followed by ring-closing metathesis is shown to be a general and powerful reaction sequence for the preparation of diverse polycyclic scaffolds from simple precursors. The modular strategy successfully constructs substructures prevalent in numerous bioactive natural product families, varying in substitution and carbocyclic composition. Several of the prepared compounds were shown to possess potent cytotoxic activity against a panel of tumor cell lines. The utility of this strategy was further demonstrated by a concise and highly convergent 17-step formal synthesis of the complex antimalarial marine diterpene, (+)-7,20-diisocyanoadociane. The stereoselective oxidative coupling of cyclic ketones via silyl bis-enol ethers followed by ring-closing metathesis is shown to be a general and powerful reaction sequence for the preparation of diverse polycyclic scaffolds from simple precursors. The modular strategy successfully constructs substructures prevalent in numerous bioactive natural product families, varying in substitution and carbocyclic composition. Several of the prepared compounds were shown to possess potent cytotoxic activity against a panel of tumor cell lines. The utility of this strategy was further demonstrated by a concise and highly convergent 17-step formal synthesis of the complex antimalarial marine diterpene, (+)-7,20-diisocyanoadociane.The stereoselective oxidative coupling of cyclic ketones via silyl bis-enol ethers followed by ring-closing metathesis is shown to be a general and powerful reaction sequence for the preparation of diverse polycyclic scaffolds from simple precursors. The modular strategy successfully constructs substructures prevalent in numerous bioactive natural product families, varying in substitution and carbocyclic composition. Several of the prepared compounds were shown to possess potent cytotoxic activity against a panel of tumor cell lines. The utility of this strategy was further demonstrated by a concise and highly convergent 17-step formal synthesis of the complex antimalarial marine diterpene, (+)-7,20-diisocyanoadociane. The stereoselective oxidative coupling of cyclic ketones via silyl bis-enol ethers followed by ring-closing metathesis is shown to be a general and powerful reaction sequence for the preparation of diverse polycyclic scaffolds from I simple precursors. The modular strategy successfully constructs substructures prevalent in numerous bioactive natural product families, varying in substitution and carbocyclic composition. Several of the prepared compounds were shown to possess potent cytotoxic activity against a panel of tumor cell lines. The utility of this strategy was further demonstrated by a concise and highly convergent 17-step formal synthesis of the complex antimalarial marine diterpene, (+)-7,20-diisocyanoadociane. |
| Author | Thomson, Regan J Robinson, Emily E |
| AuthorAffiliation | Department of Chemistry Northwestern University |
| AuthorAffiliation_xml | – name: Department of Chemistry – name: Northwestern University |
| Author_xml | – sequence: 1 givenname: Emily E surname: Robinson fullname: Robinson, Emily E – sequence: 2 givenname: Regan J orcidid: 0000-0001-5546-4038 surname: Thomson fullname: Thomson, Regan J email: r-thomson@northwestern.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/29309727$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1002/anie.201509160 10.1021/ja8075633 10.1002/anie.200902151 10.1038/nchem.2865 10.1021/ol201812n 10.1021/ja906122g 10.1021/ol990805f 10.1039/c29700000708 10.1021/jo9617326 10.1246/cl.2011.246 10.1055/s-0035-1561636 10.1021/ja00836a034 10.1021/ja0488380 10.1021/ja061660s 10.1016/S0040-4020(01)81963-3 10.1134/S1070428011050058 10.1021/ja049694s 10.1021/ja200034b 10.1039/B913880N 10.1039/C6CS00185H 10.1002/anie.200461864 10.1021/acs.orglett.5b00032 10.1021/ja00235a052 10.1039/C4SC00356J 10.1055/s-0028-1088126 10.1021/ja00447a035 10.1002/anie.201703186 10.1021/ja00747a051 10.1021/ol902400q 10.1021/jacs.6b03899 10.1021/jm901241e 10.1002/chem.201604795 10.1021/acs.joc.7b00448 10.1021/ol990909q 10.1073/pnas.96.18.10403 10.1021/ja0719428 10.1002/anie.200603024 10.1021/jo971650x 10.1021/om300393m 10.1021/ol3027363 10.1021/jo01314a052 10.1039/c1sc00357g 10.1038/s41467-017-02061-7 10.1021/np9602325 10.1038/nature12472 10.1021/jm200504p 10.1021/jacs.5b06480 10.1039/c39880000430 10.1021/ja01605a013 10.1021/ja205017e 10.1021/ja804159y 10.1126/science.1142696 10.1126/science.287.5460.1964 10.1021/ol801392d 10.1021/ol802516z 10.1039/C4NP00109E 10.2174/0929867053363351 10.1021/ol702306z 10.1586/17474086.2014.873699 10.1002/anie.201603581 10.1002/ddr.20179 10.1021/jacs.7b07706 10.1021/ol061228f 10.1038/nchem.1549 10.1002/anie.201104726 10.1021/acs.joc.6b01449 10.1002/ejoc.201200665 10.1016/j.tetlet.2014.12.075 10.1039/b104000f 10.1021/ja052939w 10.1158/1078-0432.CCR-11-2703 10.1351/pac196817030519 10.1021/ja077212h 10.1021/ja803158y 10.1039/c6cs00185h 10.1038/NCHEM.2865 10.1039/c4np00109e 10.1126/science. 1142696 10.1039/b913880n 10.1039/c4sc00356j |
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| Keywords | CARBON BOND FORMATION OXIDATION CATALYSIS ESTERS LEADS INHIBITOR ENANTIOSELECTIVE TOTAL-SYNTHESIS 1,4-DIKETONES |
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| References | ref9/cit9 ref45/cit45 ref3/cit3 ref27/cit27 ref63/cit63 ref56/cit56 ref16/cit16 ref52/cit52 ref23/cit23 ref8/cit8 ref31/cit31 ref59/cit59 ref2/cit2 ref34/cit34 ref71/cit71 ref37/cit37 ref20/cit20 ref48/cit48 ref60/cit60 ref74/cit74 ref17/cit17 ref10/cit10 ref35/cit35 ref53/cit53 ref19/cit19 ref21/cit21 ref42/cit42 ref46/cit46 ref49/cit49 ref13/cit13 ref61/cit61 ref75/cit75 ref67/cit67 ref24/cit24 ref38/cit38 Ivanoff D. (ref22/cit22) 1935; 2 ref50/cit50 ref64/cit64 ref54/cit54 ref6/cit6 ref36/cit36 ref18/cit18 ref65/cit65 ref11/cit11 ref25/cit25 ref29/cit29 ref72/cit72 ref76/cit76 ref32/cit32 ref39/cit39 ref14/cit14 ref57/cit57 ref5/cit5 ref51/cit51 ref43/cit43 ref28/cit28 ref40/cit40 ref68/cit68 ref26/cit26 ref55/cit55 ref73/cit73 ref69/cit69 ref12/cit12 ref15/cit15 ref62/cit62 ref66/cit66 ref41/cit41 ref58/cit58 ref33/cit33 ref4/cit4 ref30/cit30 ref47/cit47 ref44/cit44 Corey E. J. (ref1/cit1) 1989 ref70/cit70 ref7/cit7 Kim, WS (WOS:000423143500015) 2018; 10 Paciaroni, NG (WOS:000399314800014) 2017; 23 FRAZIER, RH (WOS:A1980KV39700052) 1980; 45 Kou, KGM (WOS:000412716900050) 2017; 139 Nicolaou, KC (WOS:000269979100004) 2009; 48 Ivanoff, D. (000424851500052.38) 1935; 2 Moeller, KD (WOS:000269443700002) 2009 Pronin, SV (WOS:000324244900035) 2013; 501 COREY, EJ (WOS:A1956WB84700013) 1956; 78 RATHKE, MW (WOS:A1971K242800052) 1971; 93 Lovering, F (WOS:000271427900027) 2009; 52 Fairweather, KA (WOS:000239001500060) 2006; 8 Daub, ME (WOS:000401044700002) 2017; 82 Beeson, TD (WOS:000245983100040) 2007; 316 Csalcy, A. G. (000424851500052.18) 2001; 30 Quesnelle, CA (WOS:000384041500018) 2016; 27 ITO, Y (WOS:A1975V465900034) 1975; 97 Furrow, ME (WOS:000221135400030) 2004; 126 Moreau, P (WOS:000335328500011) 2014; 7 COREY, EJ (WOS:A1987F589700052) 1987; 109 Guo, FH (WOS:000308294700001) 2012; 2012 Wright, AD (WOS:A1996UZ99400020) 1996; 59 Schreiber, SL (WOS:000085902800047) 2000; 287 Torosyan, SA (WOS:000291487300005) 2011; 47 Du, JN (WOS:000295732200006) 2011; 2 Schmittel, M (WOS:000071798200037) 1998; 63 Yamamoto, E (WOS:000312564500016) 2012; 14 Shaw, MH (WOS:000381847600002) 2016; 81 Kim, H (WOS:000252292500007) 2008; 130 ITO, Y (WOS:A1977CX09000035) 1977; 99 Herzon, SB (WOS:000290782200007) 2011; 133 Asaba, T (WOS:000367724000046) 2015; 54 Hong, DS (WOS:000307502100020) 2012; 18 Wildermuth, R (WOS:000417702300034) 2017; 8 Banos, M. T. (000424851500052.5) 1997; 62 Baran, PS (WOS:000226537300018) 2005; 44 Scholl, M (WOS:000085171700034) 1999; 1 Casey, BM (WOS:000293872800025) 2011; 133 ASAOKA, M (WOS:A1990CU58200008) 1990; 46 Konkol, LC (WOS:000296207100029) 2011; 50 You, L (WOS:000359962000024) 2015; 137 Lu, HH (WOS:000378193300016) 2016; 138 Hong, SH (WOS:000233917500016) 2005; 127 Baran, PS (WOS:000238590000056) 2006; 128 Roosen, PC (WOS:000382790600027) 2016; 55 Miyaoka, H (WOS:000288643400009) 2011; 40 Jang, HY (WOS:000246843600020) 2007; 129 Martin, CL (WOS:000256671400026) 2008; 130 DeMartino, MP (WOS:000258660600055) 2008; 130 Corey, E. J. (000424851500052.16) 1989 Corrigan, N (WOS:000387978000007) 2016; 45 Walters, WP (WOS:000295546200001) 2011; 54 WOODWARD R B (BCI:BCI196905061519) 1968; 17 Vega, MM (WOS:000356544800063) 2015; 56 Clift, MD (WOS:000271271500099) 2009; 131 Hong, SH (WOS:000222120900001) 2004; 126 Do, HQ (WOS:000311466300011) 2012; 31 Scott, SK (WOS:000404140900013) 2017; 56 ASAOKA, M (WOS:A1988N351100016) 1988 Huigens Iii, R W. (000424851500052.35) 2013; 5 Sarakinos, G (WOS:000085171500033) 1999; 1 Graham, TH (WOS:000263320200026) 2008; 130 Sporn, MB (WOS:000250912200005) 2007; 68 Narayanam, JMR (WOS:000285390900008) 2011; 40 Bolze, P (WOS:000258833700026) 2008; 10 Konkol, LC (WOS:000272038200048) 2009; 11 MATTHEWS, RS (WOS:A1970G493400085) 1970 Meng, LH (WOS:000082424100084) 1999; 96 Ghosh, S (WOS:000351558100007) 2015; 17 Avetta, CT (WOS:000261613700031) 2008; 10 Baran, PS (WOS:000241976300035) 2006; 45 Jones, BT (WOS:000334492700013) 2014; 5 Ekebergh, A (WOS:000293759100078) 2011; 13 Clift, MD (WOS:000250302000067) 2007; 9 Schnermann, MJ (WOS:000351710900003) 2015; 32 Guo, Z (WOS:000226070200003) 2005; 12 |
| References_xml | – ident: ref48/cit48 doi: 10.1002/anie.201509160 – ident: ref30/cit30 doi: 10.1021/ja8075633 – ident: ref70/cit70 doi: 10.1002/anie.200902151 – ident: ref7/cit7 doi: 10.1038/nchem.2865 – ident: ref18/cit18 doi: 10.1021/ol201812n – ident: ref38/cit38 doi: 10.1021/ja906122g – ident: ref43/cit43 doi: 10.1021/ol990805f – ident: ref76/cit76 doi: 10.1039/c29700000708 – ident: ref49/cit49 doi: 10.1021/jo9617326 – ident: ref64/cit64 doi: 10.1246/cl.2011.246 – ident: ref21/cit21 doi: 10.1055/s-0035-1561636 – ident: ref24/cit24 doi: 10.1021/ja00836a034 – ident: ref53/cit53 doi: 10.1021/ja0488380 – ident: ref14/cit14 doi: 10.1021/ja061660s – ident: ref44/cit44 doi: 10.1016/S0040-4020(01)81963-3 – ident: ref46/cit46 doi: 10.1134/S1070428011050058 – ident: ref47/cit47 doi: 10.1021/ja049694s – ident: ref17/cit17 doi: 10.1021/ja200034b – ident: ref72/cit72 doi: 10.1039/B913880N – volume-title: The Logic of Chemical Synthesis year: 1989 ident: ref1/cit1 – ident: ref73/cit73 doi: 10.1039/C6CS00185H – ident: ref13/cit13 doi: 10.1002/anie.200461864 – ident: ref20/cit20 doi: 10.1021/acs.orglett.5b00032 – ident: ref63/cit63 doi: 10.1021/ja00235a052 – ident: ref40/cit40 doi: 10.1039/C4SC00356J – ident: ref33/cit33 doi: 10.1055/s-0028-1088126 – ident: ref25/cit25 doi: 10.1021/ja00447a035 – ident: ref9/cit9 doi: 10.1002/anie.201703186 – ident: ref23/cit23 doi: 10.1021/ja00747a051 – ident: ref37/cit37 doi: 10.1021/ol902400q – ident: ref67/cit67 doi: 10.1021/jacs.6b03899 – ident: ref3/cit3 doi: 10.1021/jm901241e – ident: ref8/cit8 doi: 10.1002/chem.201604795 – ident: ref62/cit62 doi: 10.1021/acs.joc.7b00448 – ident: ref51/cit51 doi: 10.1021/ol990909q – ident: ref58/cit58 doi: 10.1073/pnas.96.18.10403 – ident: ref28/cit28 doi: 10.1021/ja0719428 – ident: ref26/cit26 doi: 10.1002/anie.200603024 – ident: ref34/cit34 doi: 10.1021/jo971650x – ident: ref32/cit32 doi: 10.1021/om300393m – ident: ref50/cit50 doi: 10.1021/ol3027363 – ident: ref52/cit52 doi: 10.1021/jo01314a052 – ident: ref71/cit71 doi: 10.1039/c1sc00357g – ident: ref10/cit10 doi: 10.1038/s41467-017-02061-7 – ident: ref60/cit60 doi: 10.1021/np9602325 – ident: ref68/cit68 doi: 10.1038/nature12472 – ident: ref2/cit2 doi: 10.1021/jm200504p – ident: ref19/cit19 doi: 10.1021/jacs.5b06480 – ident: ref45/cit45 doi: 10.1039/c39880000430 – ident: ref75/cit75 doi: 10.1021/ja01605a013 – ident: ref27/cit27 doi: 10.1021/ja205017e – ident: ref15/cit15 doi: 10.1021/ja804159y – ident: ref29/cit29 doi: 10.1126/science.1142696 – ident: ref4/cit4 doi: 10.1126/science.287.5460.1964 – ident: ref42/cit42 doi: 10.1021/ol801392d – ident: ref36/cit36 doi: 10.1021/ol802516z – ident: ref61/cit61 doi: 10.1039/C4NP00109E – ident: ref57/cit57 doi: 10.2174/0929867053363351 – ident: ref35/cit35 doi: 10.1021/ol702306z – ident: ref59/cit59 doi: 10.1586/17474086.2014.873699 – ident: ref65/cit65 doi: 10.1002/anie.201603581 – ident: ref56/cit56 doi: 10.1002/ddr.20179 – ident: ref6/cit6 doi: 10.1021/jacs.7b07706 – ident: ref66/cit66 doi: 10.1021/ol061228f – ident: ref5/cit5 doi: 10.1038/nchem.1549 – ident: ref39/cit39 doi: 10.1002/anie.201104726 – ident: ref74/cit74 doi: 10.1021/acs.joc.6b01449 – ident: ref11/cit11 doi: 10.1002/ejoc.201200665 – volume: 2 start-page: 76 year: 1935 ident: ref22/cit22 publication-title: Bull. Soc. Chim. Fr. – ident: ref41/cit41 doi: 10.1016/j.tetlet.2014.12.075 – ident: ref12/cit12 doi: 10.1039/b104000f – ident: ref54/cit54 doi: 10.1021/ja052939w – ident: ref55/cit55 doi: 10.1158/1078-0432.CCR-11-2703 – ident: ref69/cit69 doi: 10.1351/pac196817030519 – ident: ref31/cit31 doi: 10.1021/ja077212h – ident: ref16/cit16 doi: 10.1021/ja803158y – year: 1989 ident: 000424851500052.16 publication-title: The Logic of Chemical Synthesis – volume: 133 start-page: 11492 year: 2011 ident: WOS:000293872800025 article-title: On the Nature of the Oxidative Heterocoupling of Lithium Enolates publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja205017e – volume: 130 start-page: 7568 year: 2008 ident: WOS:000256671400026 article-title: Total synthesis of (+/-)-actinophyllic acid publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja803158y – volume: 45 start-page: 6165 year: 2016 ident: WOS:000387978000007 article-title: Photocatalysis in organic and polymer synthesis publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/c6cs00185h – volume: 130 start-page: 398 year: 2008 ident: WOS:000252292500007 article-title: Enantioselective organo-SOMO catalysis: The alpha-vinylation of aldehydes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja077212h – volume: 45 start-page: 5408 year: 1980 ident: WOS:A1980KV39700052 article-title: OXIDATIVE COUPLING OF KETONE ENOLATES BY FERRIC-CHLORIDE publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 12 start-page: 173 year: 2005 ident: WOS:000226070200003 article-title: Biologically active quassinoids and their chemistry: Potential leads for drug design publication-title: CURRENT MEDICINAL CHEMISTRY – volume: 99 start-page: 1487 year: 1977 ident: WOS:A1977CX09000035 article-title: SYNTHESIS OF 1,4-DIKETONES BY OXIDATIVE COUPLING OF KETONE ENOLATES WITH CUCL2 publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 81 start-page: 6898 year: 2016 ident: WOS:000381847600002 article-title: Photoredox Catalysis in Organic Chemistry publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.6b01449 – start-page: 1208 year: 2009 ident: WOS:000269443700002 article-title: Intramolecular Anodic Olefin Coupling Reactions: Using Radical Cation Intermediates to Trigger New Umpolung Reactions publication-title: SYNLETT doi: 10.1055/s-0028-1088126 – volume: 44 start-page: 606 year: 2005 ident: WOS:000226537300018 article-title: Short, enantioselective total synthesis of Stephacidin A publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200461864 – volume: 287 start-page: 1964 year: 2000 ident: WOS:000085902800047 article-title: Target-oriented and diversity-oriented organic synthesis in drug discovery publication-title: SCIENCE – volume: 10 start-page: 70 year: 2018 ident: WOS:000423143500015 article-title: Synthetic nat- or ent-steroids in as few as five chemical steps from epichlorohydrin publication-title: NATURE CHEMISTRY doi: 10.1038/NCHEM.2865 – volume: 62 start-page: 3984 year: 1997 ident: 000424851500052.5 publication-title: J. Org. Chem. – volume: 109 start-page: 287 year: 1987 ident: WOS:A1987F589700052 article-title: TOTAL SYNTHESIS AND ABSOLUTE-CONFIGURATION OF 7,20-DIISOCYANOADOCIANE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 7 start-page: 265 year: 2014 ident: WOS:000335328500011 article-title: The emerging role of carfilzomib combination therapy in the management of multiple myeloma publication-title: EXPERT REVIEW OF HEMATOLOGY doi: 10.1586/17474086.2014.873699 – volume: 55 start-page: 7180 year: 2016 ident: WOS:000382790600027 article-title: A Formal Enantiospecific Synthesis of 7,20-Diisocyanoadociane publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201603581 – volume: 1 start-page: 811 year: 1999 ident: WOS:000085171500033 article-title: Simple and practical routes to enantiomerically pure 5-(trialkylsilyl)-2-cyclohexenones publication-title: ORGANIC LETTERS – volume: 32 start-page: 543 year: 2015 ident: WOS:000351710900003 article-title: Syntheses and biological studies of marine terpenoids derived from inorganic cyanide publication-title: NATURAL PRODUCT REPORTS doi: 10.1039/c4np00109e – volume: 9 start-page: 4667 year: 2007 ident: WOS:000250302000067 article-title: Oxidative carbon-carbon bond formation via silyl bis-enol ethers: Controlled cross-coupling for the synthesis of quaternary centers publication-title: ORGANIC LETTERS doi: 10.1021/ol702306z – start-page: 708 year: 1970 ident: WOS:A1970G493400085 article-title: STEREOCHEMISTRY OF ENOLATE ALKYLATION - ANGULAR SUBSTITUENT EFFECTS publication-title: JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS – volume: 17 start-page: 519 year: 1968 ident: BCI:BCI196905061519 article-title: RECENT ADVANCES IN THE CHEMISTRY OF NATURAL PRODUCTS publication-title: Pure and Applied Chemistry – volume: 126 start-page: 5436 year: 2004 ident: WOS:000221135400030 article-title: Practical procedures for the preparation of N-tert-butyldimethylsilylhydrazones and their use in modified Wolff-Kishner reductions and in the synthesis of vinyl halides and gem-dihalides publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja049694s – volume: 130 start-page: 16494 year: 2008 ident: WOS:000263320200026 article-title: Enantioselective Organo-Singly Occupied Molecular Orbital Catalysis: The Carbo-oxidation of Styrenes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja8075633 – volume: 47 start-page: 682 year: 2011 ident: WOS:000291487300005 article-title: Oxidation of (1S,5R,7R,S)-(4,7-dimethyl-6-oxabicyclo[3.2.1]oct-3-en-7-yl) methanol with pyridinium chlorochromate publication-title: RUSSIAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1134/S1070428011050058 – volume: 56 start-page: 8125 year: 2017 ident: WOS:000404140900013 article-title: An Enyne Cope Rearrangement Enables Polycycloalkane Synthesis from Readily Available Starting Materials publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201703186 – volume: 501 start-page: 195 year: 2013 ident: WOS:000324244900035 article-title: Stereoinversion of tertiary alcohols to tertiary-alkyl isonitriles and amines publication-title: NATURE doi: 10.1038/nature12472 – volume: 10 start-page: 3753 year: 2008 ident: WOS:000258833700026 article-title: Organocatalytic asymmetric synthesis of 5-(trialkylsilyl)cyclohex-2-enones and the transformation into useful building blocks publication-title: ORGANIC LETTERS doi: 10.1021/ol801392d – volume: 31 start-page: 7816 year: 2012 ident: WOS:000311466300011 article-title: Copper-Catalyzed Homodimerization of Nitronates and Enolates under an Oxygen Atmosphere publication-title: ORGANOMETALLICS doi: 10.1021/om300393m – volume: 46 start-page: 1541 year: 1990 ident: WOS:A1990CU58200008 article-title: DIASTEREOSELECTIVE 1,4-ADDITION OF VARIOUS NUCLEOPHILES TO 5-TRIMETHYLSILYL-2-CYCLOHEXENONE - SYNTHESIS OF (+)-RAMULOSIN publication-title: TETRAHEDRON – volume: 96 start-page: 10403 year: 1999 ident: WOS:000082424100084 article-title: Epoxomicin, a potent and selective proteasome inhibitor, exhibits in vivo antiinflammatory activity publication-title: PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA – volume: 40 start-page: 246 year: 2011 ident: WOS:000288643400009 article-title: A Formal Synthesis of Antimalarial Diterpenoid 7,20-Diisocyanoadociane publication-title: CHEMISTRY LETTERS doi: 10.1246/cl.2011.246 – volume: 54 start-page: 6405 year: 2011 ident: WOS:000295546200001 article-title: What Do Medicinal Chemists Actually Make? A 50-Year Retrospective publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/jm200504p – volume: 5 start-page: 195 year: 2013 ident: 000424851500052.35 publication-title: Nat. Chem. – volume: 50 start-page: 9931 year: 2011 ident: WOS:000296207100029 article-title: Enantioselective Total Synthesis and Studies into the Configurational Stability of Bismurrayaquinone A publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201104726 – volume: 23 start-page: 4327 year: 2017 ident: WOS:000399314800014 article-title: A Tryptoline Ring-Distortion Strategy Leads to Complex and Diverse Biologically Active Molecules from the Indole Alkaloid Yohimbine publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201604795 – volume: 17 start-page: 1373 year: 2015 ident: WOS:000351558100007 article-title: Oxidative Dimerization of 2-Oxindoles Promoted by (KOBu)-Bu-t-l(2): Total Synthesis of (+/-)-Folicanthine publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.5b00032 – volume: 129 start-page: 7004 year: 2007 ident: WOS:000246843600020 article-title: Enantioselective organocatalytic singly occupied molecular orbital activation: The enantioselective alpha-enolation of aldehydes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja0719428 – volume: 316 start-page: 582 year: 2007 ident: WOS:000245983100040 article-title: Enantioselective organocatalysis using SOMO activation publication-title: SCIENCE doi: 10.1126/science. 1142696 – volume: 97 start-page: 649 year: 1975 ident: WOS:A1975V465900034 article-title: SYNTHESIS OF 1,4-DIKETONES BY REACTION OF SILYL ENOL ETHER WITH AG2O - REGIOSPECIFIC FORMATION OF SILVER(I) ENOLATE INTERMEDIATES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 11 start-page: 5550 year: 2009 ident: WOS:000272038200048 article-title: Oxidative Carbon-Carbon Bond Formation via Allyldimethylsilyl Enol Ethers publication-title: ORGANIC LETTERS doi: 10.1021/ol902400q – volume: 54 start-page: 14457 year: 2015 ident: WOS:000367724000046 article-title: Total Synthesis of Crotophorbolone publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201509160 – volume: 131 start-page: 14579 year: 2009 ident: WOS:000271271500099 article-title: Development of a Merged Conjugate Addition/Oxidative Coupling Sequence. Application to the Enantioselective Total Synthesis of Metacycloprodigiosin and Prodigiosin R1 publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja906122g – volume: 56 start-page: 3228 year: 2015 ident: WOS:000356544800063 article-title: Enantioselective synthesis of metacycloprodigiosin via the 'Wasserman pyrrole' publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2014.12.075 – volume: 137 start-page: 10120 year: 2015 ident: WOS:000359962000024 article-title: Asymmetric Total Synthesis of Propindilactone G publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.5b06480 – volume: 126 start-page: 7414 year: 2004 ident: WOS:000222120900001 article-title: Decomposition of a key intermediate in ruthenium-catalyzed olefin metathesis reactions publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja0488380 – volume: 30 start-page: 313 year: 2001 ident: 000424851500052.18 publication-title: Chem. Soc. Rev. – volume: 2 start-page: 76 year: 1935 ident: 000424851500052.38 publication-title: Bull. Soc. Chim. Fr. – volume: 82 start-page: 4533 year: 2017 ident: WOS:000401044700002 article-title: General Approaches to Structurally Diverse Isocyanoditerpenes publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.7b00448 – volume: 27 start-page: 2254 year: 2016 ident: WOS:000384041500018 article-title: A Practical Approach for Enantio- and Diastereocontrol in the Synthesis of 2,3-Disubstituted Succinic Acid Esters: Synthesis of the pan-Notch Inhibitor BMS-906024 publication-title: SYNLETT doi: 10.1055/s-0035-1561636 – volume: 68 start-page: 174 year: 2007 ident: WOS:000250912200005 article-title: Platforms and networks in triterpenoid pharmacology publication-title: DRUG DEVELOPMENT RESEARCH doi: 10.1002/ddr.20179 – volume: 45 start-page: 7083 year: 2006 ident: WOS:000241976300035 article-title: Intermolecular oxidative enolate heterocoupling publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200603024 – volume: 40 start-page: 102 year: 2011 ident: WOS:000285390900008 article-title: Visible light photoredox catalysis: applications in organic synthesis publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/b913880n – volume: 127 start-page: 17160 year: 2005 ident: WOS:000233917500016 article-title: Prevention of undesirable isomerization during olefin metathesis publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja052939w – start-page: 430 year: 1988 ident: WOS:A1988N351100016 article-title: SYNTHESIS OF CHIRAL 5-SUBSTITUTED CYCLOHEX-2-ENONES FROM 5-TRIMETHYLSILYLCYCLOHEX-2-ENONE publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS – volume: 13 start-page: 4458 year: 2011 ident: WOS:000293759100078 article-title: Oxidative Coupling as a Biomimetic Approach to the Synthesis of Scytonemin publication-title: ORGANIC LETTERS doi: 10.1021/ol201812n – volume: 63 start-page: 396 year: 1998 ident: WOS:000071798200037 article-title: Diastereoselective enolate coupling through redox umpolung in silicon and titanium bisenolates: A novel concept based on intramolecularization of carbon-carbon bond formation publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 2 start-page: 2115 year: 2011 ident: WOS:000295732200006 article-title: Photocatalytic reductive cyclizations of enones: Divergent reactivity of photogenerated radical and radical anion intermediates publication-title: CHEMICAL SCIENCE doi: 10.1039/c1sc00357g – volume: 93 start-page: 4605 year: 1971 ident: WOS:A1971K242800052 article-title: REACTION OF ESTER ENOLATES WITH COPPER(II) SALTS - SYNTHESIS OF SUBSTITUTED SUCCINATE ESTERS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 48 start-page: 7140 year: 2009 ident: WOS:000269979100004 article-title: Samarium Diiodide Mediated Reactions in Total Synthesis publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200902151 – volume: 138 start-page: 7268 year: 2016 ident: WOS:000378193300016 article-title: Synthesis of (+)-7,20-Diisocyanoadociane and Liver -Stage Antiplasmodial Activity of the Isocyanoterpene Class publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.6b03899 – volume: 2012 start-page: 4881 year: 2012 ident: WOS:000308294700001 article-title: Oxidative Coupling of Enolates, Enol Silanes, and Enamines: Methods and Natural Product Synthesis publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.201200665 – volume: 14 start-page: 6178 year: 2012 ident: WOS:000312564500016 article-title: Hydrolytic Enantioselective Protonation of Cyclic Dienyl Esters and a beta-Diketone with Chiral Phase-Transfer Catalysts publication-title: ORGANIC LETTERS doi: 10.1021/ol3027363 – volume: 78 start-page: 6269 year: 1956 ident: WOS:A1956WB84700013 article-title: STEREOELECTRONIC CONTROL IN ENOLIZATION-KETONIZATION REACTIONS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 8 start-page: 3395 year: 2006 ident: WOS:000239001500060 article-title: A formal total synthesis of the marine diterpenoid diisocyanoadociane publication-title: ORGANIC LETTERS doi: 10.1021/ol061228f – volume: 133 start-page: 7260 year: 2011 ident: WOS:000290782200007 article-title: 11-Step Enantioselective Synthesis of (-)-Lomaiviticin Aglycon publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja200034b – volume: 8 start-page: ARTN 2083 year: 2017 ident: WOS:000417702300034 article-title: A modular synthesis of tetracyclic meroterpenoid antibiotics publication-title: NATURE COMMUNICATIONS doi: 10.1038/s41467-017-02061-7 – volume: 1 start-page: 953 year: 1999 ident: WOS:000085171700034 article-title: Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands publication-title: ORGANIC LETTERS – volume: 128 start-page: 8678 year: 2006 ident: WOS:000238590000056 article-title: Enantioselective total synthesis of avrainvillamide and the stephacidins publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja061660s – volume: 139 start-page: 13882 year: 2017 ident: WOS:000412716900050 article-title: A Unifying Synthesis Approach to the C-18-, C-19-, and C-20-Diterpenoid Alkaloids publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.7b07706 – volume: 5 start-page: 1794 year: 2014 ident: WOS:000334492700013 article-title: Total synthesis of propolisbenzofuran B publication-title: CHEMICAL SCIENCE doi: 10.1039/c4sc00356j – volume: 59 start-page: 710 year: 1996 ident: WOS:A1996UZ99400020 article-title: Antimalarial activity: The search for marine-derived natural products with selective antimalarial activity publication-title: JOURNAL OF NATURAL PRODUCTS – volume: 130 start-page: 11546 year: 2008 ident: WOS:000258660600055 article-title: Intermolecular enolate heterocoupling: Scope, mechanism, and application publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja804159y – volume: 18 start-page: 3396 year: 2012 ident: WOS:000307502100020 article-title: A Phase I First-in-Human Trial of Bardoxolone Methyl in Patients with Advanced Solid Tumors and Lymphomas publication-title: CLINICAL CANCER RESEARCH doi: 10.1158/1078-0432.CCR-11-2703 – volume: 52 start-page: 6752 year: 2009 ident: WOS:000271427900027 article-title: Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/jm901241e – volume: 10 start-page: 5621 year: 2008 ident: WOS:000261613700031 article-title: Diastereoselective Oxidative Carbon-Carbon Bond Formation via Silyl Bis-enol Ethers publication-title: ORGANIC LETTERS doi: 10.1021/ol802516z |
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| Snippet | The stereoselective oxidative coupling of cyclic ketones via silyl bis-enol ethers followed by ring-closing metathesis is shown to be a general and powerful... |
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| SubjectTerms | antimalarials cell lines Chemistry Chemistry, Multidisciplinary cytotoxicity diterpenoids ethers ketones neoplasm cells Physical Sciences Science & Technology stereoselectivity |
| Title | A Strategy for the Convergent and Stereoselective Assembly of Polycyclic Molecules |
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