Efficient Total Syntheses of (−)-Colombiasin A and (−)-Elisapterosin B: Application of the Cr-Catalyzed Asymmetric Quinone Diels-Alder Reaction
A made‐to‐order asymmetric catalytic reaction was applied in the key quinone Diels–Alder step of the total syntheses of the title compounds (see scheme for the synthesis of colombiasin A). The reaction was highly regio‐ and diastereoselective.
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| Published in | Angewandte Chemie International Edition Vol. 44; no. 37; pp. 6046 - 6050 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
19.09.2005
WILEY‐VCH Verlag Wiley |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1433-7851 1521-3773 |
| DOI | 10.1002/anie.200502178 |
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| Abstract | A made‐to‐order asymmetric catalytic reaction was applied in the key quinone Diels–Alder step of the total syntheses of the title compounds (see scheme for the synthesis of colombiasin A). The reaction was highly regio‐ and diastereoselective. |
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| AbstractList | A made‐to‐order asymmetric catalytic reaction was applied in the key quinone Diels–Alder step of the total syntheses of the title compounds (see scheme for the synthesis of colombiasin A). The reaction was highly regio‐ and diastereoselective. |
| Author | Jarvo, Elizabeth R. Lawrence, Brian M. Boezio, Alessandro A. Jacobsen, Eric N. |
| Author_xml | – sequence: 1 givenname: Alessandro A. surname: Boezio fullname: Boezio, Alessandro A. organization: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA, Fax: (+1) 617-496-1880 – sequence: 2 givenname: Elizabeth R. surname: Jarvo fullname: Jarvo, Elizabeth R. organization: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA, Fax: (+1) 617-496-1880 – sequence: 3 givenname: Brian M. surname: Lawrence fullname: Lawrence, Brian M. organization: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA, Fax: (+1) 617-496-1880 – sequence: 4 givenname: Eric N. surname: Jacobsen fullname: Jacobsen, Eric N. email: jacobsen@chemistry.harvard.edu organization: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA, Fax: (+1) 617-496-1880 |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/16108082$$D View this record in MEDLINE/PubMed |
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| Copyright | Copyright © 2005 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim |
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| Issue | 37 |
| Keywords | natural products cycloaddition metathesis PSEUDOPTEROGORGIA-ELISABETHAE STRATEGY TETRACYCLIC FRAMEWORK quinones asymmetric catalysis TERPENOIDS DITERPENE |
| Language | English |
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| Notes | istex:289512F2E86F9D4D707F02EDF3320B57DB7D50E4 ArticleID:ANIE200502178 ark:/67375/WNG-9BZVDGBX-8 This work was supported by the NIH (GM-59316). We are grateful to Dr. R. Staples for carrying out the X-ray crystal structure analyses. This work was supported by the NIH (GM‐59316). We are grateful to Dr. R. Staples for carrying out the X‐ray crystal structure analyses. Medline NIH RePORTER ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
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Formation of isomer 13′, wherein the olefin has isomerized to the tetrasubstituted silyl enol ether, presumably occurs during chromatographic purification. Analogous isomerizations are not observed with less hindered cycloadducts. See Supporting Information for details. For an example of isomerization of a silyl enol ether upon exposure to silica gel, see: P. Magnus, I. S. Mitchell, Tetrahedron Lett. 1998, 39, 9131-9134. A. D. Rodríguez, E. Gonzalez, S. D. Huang, J. Org. Chem. 1998, 63, 7083-7091. Angew. Chem. Int. Ed. 2004, 43, 4837-4841 P. Villiers, N. Vicart, Y. Ramondenc, G. Ple, Tetrahedron Lett. 1999, 40, 8781-8784. elisabethin A: T. J. Heckrodt, J. Mulzer, J. Am. Chem. Soc. 2003, 125, 4680-4681 elisapterosin B: D. C. Harrowven, D. D. Pascoe, D. Demurtas, H. O. Bourne, Angew. Chem. 2005, 117, 1247-1248 elisapterosin B: A. I. Kim, S. D. Rychnovsky, Angew. Chem. 2003, 115, 1305-1308 A. D. Rodríguez, Y.-P. Shi, Tetrahedron 2000, 56, 9015-9023 1995; 51 2004 2004; 116 43 1990; 55 1991; 113 2002 2002; 114 41 1986; 51 2002; 74 2000; 65 2004; 67 1995 2002; 4 2000; 2 2003 1999; 40 1998; 63 2001; 42 2002; 28 1998; 39 2003 2003; 115 42 2000; 56 2001 2001; 113 40 2002; 240 2005; 127 1989; 364 2005; 7 2003; 5 2003; 1 2003; 125 2005 2005; 117 44 e_1_2_2_24_2 e_1_2_2_47_2 e_1_2_2_4_2 e_1_2_2_22_2 e_1_2_2_49_2 e_1_2_2_6_2 e_1_2_2_20_2 e_1_2_2_2_2 press; in (e_1_2_2_28_3) 2005; 44 e_1_2_2_41_2 e_1_2_2_8_2 e_1_2_2_28_2 e_1_2_2_43_2 e_1_2_2_26_2 e_1_2_2_45_2 e_1_2_2_36_2 e_1_2_2_11_2 e_1_2_2_38_2 e_1_2_2_51_2 e_1_2_2_19_2 e_1_2_2_30_2 e_1_2_2_17_2 e_1_2_2_32_2 e_1_2_2_15_3 e_1_2_2_15_2 e_1_2_2_3_2 e_1_2_2_23_2 e_1_2_2_48_2 e_1_2_2_5_2 e_1_2_2_21_2 e_1_2_2_1_2 e_1_2_2_40_2 e_1_2_2_29_3 e_1_2_2_29_2 e_1_2_2_42_2 e_1_2_2_7_2 e_1_2_2_27_2 e_1_2_2_44_2 e_1_2_2_9_2 e_1_2_2_25_2 e_1_2_2_46_2 e_1_2_2_12_3 e_1_2_2_12_2 e_1_2_2_37_2 e_1_2_2_10_2 e_1_2_2_39_2 e_1_2_2_50_2 e_1_2_2_18_2 e_1_2_2_31_2 e_1_2_2_16_3 e_1_2_2_16_2 e_1_2_2_33_2 e_1_2_2_14_3 e_1_2_2_14_2 e_1_2_2_35_2 Nicolaou K. 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| Snippet | A made‐to‐order asymmetric catalytic reaction was applied in the key quinone Diels–Alder step of the total syntheses of the title compounds (see scheme for the... |
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| SubjectTerms | asymmetric catalysis Benzoquinones - chemistry Bridged-Ring Compounds - chemical synthesis Chemistry Chemistry, Multidisciplinary Chromium - chemistry cycloaddition Diterpenes - chemical synthesis metathesis Models, Molecular natural products Physical Sciences quinones Science & Technology Stereoisomerism |
| Title | Efficient Total Syntheses of (−)-Colombiasin A and (−)-Elisapterosin B: Application of the Cr-Catalyzed Asymmetric Quinone Diels-Alder Reaction |
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