Rhodium(III)-Catalyzed Intramolecular Annulation through CH Activation: Total Synthesis of (±)-Antofine, (±)-Septicine, (±)-Tylophorine, and Rosettacin
Annulation: The efficient synthesis of 3‐hydroxyalkyl isoquinolones and 6‐hydroxyalkyl 2‐pyridones is enabled through the intramolecular annulation of alkyne‐tethered hydroxamic esters (see scheme, Cp*=pentamethylcyclopentadienyl). The reaction features high regioselectivity, broad substrate scope,...
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| Published in | Angewandte Chemie International Edition Vol. 51; no. 37; pp. 9372 - 9376 |
|---|---|
| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
10.09.2012
WILEY‐VCH Verlag Wiley |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1433-7851 1521-3773 1521-3773 |
| DOI | 10.1002/anie.201204970 |
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| Abstract | Annulation: The efficient synthesis of 3‐hydroxyalkyl isoquinolones and 6‐hydroxyalkyl 2‐pyridones is enabled through the intramolecular annulation of alkyne‐tethered hydroxamic esters (see scheme, Cp*=pentamethylcyclopentadienyl). The reaction features high regioselectivity, broad substrate scope, and excellent functional‐group tolerance, proceeds under mild reaction conditions with low catalyst loading, and obviates the need for an external oxidant. |
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| AbstractList | Annulation: The efficient synthesis of 3‐hydroxyalkyl isoquinolones and 6‐hydroxyalkyl 2‐pyridones is enabled through the intramolecular annulation of alkyne‐tethered hydroxamic esters (see scheme, Cp*=pentamethylcyclopentadienyl). The reaction features high regioselectivity, broad substrate scope, and excellent functional‐group tolerance, proceeds under mild reaction conditions with low catalyst loading, and obviates the need for an external oxidant. |
| Author | Park, Cheol-Min Liu, Yu Xu, Xianxiu |
| Author_xml | – sequence: 1 givenname: Xianxiu surname: Xu fullname: Xu, Xianxiu organization: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore) – sequence: 2 givenname: Yu surname: Liu fullname: Liu, Yu organization: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore) – sequence: 3 givenname: Cheol-Min surname: Park fullname: Park, Cheol-Min email: cmpark@ntu.edu.sg organization: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore) |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/22907635$$D View this record in MEDLINE/PubMed |
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| Keywords | isoquinolones HIGHLY SUBSTITUTED PYRROLES INDOLIZIDINE C?H activation ALKYNES 2-pyridones ISOQUINOLONE SYNTHESIS H ACTIVATION annulation QUINOLIZIDINE ALKALOIDS BIOLOGICAL EVALUATION DIAZO OXIME ETHERS N BOND FORMATION CATALYZED OXIDATIVE COUPLING/CYCLIZATION rhodium |
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| Notes | ark:/67375/WNG-H5GZ1RRT-F ArticleID:ANIE201204970 istex:D12262FBE2168B59E0D2642931509D88C96DFACC Nanyang Technological University We gratefully acknowledge the Nanyang Technological University for the funding of this research. We thank Dr. Rakesh Ganguly for X-ray crystallographic analysis. We gratefully acknowledge the Nanyang Technological University for the funding of this research. We thank Dr. Rakesh Ganguly for X‐ray crystallographic analysis. These authors contributed equally to this work. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
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| PublicationDate | September 10, 2012 |
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(000308399500031.48) 2008; 120 Guimond, N (WOS:000269379600015) 2009; 131 Stuart, DR (WOS:000285818700052) 2010; 132 Fox, BM (WOS:000184084800012) 2003; 46 Morimoto, K (WOS:000277212800045) 2010; 12 Rakshit, S (WOS:000288291300006) 2011; 133 Niphakis, MJ (WOS:000281180100030) 2010; 75 Huestis, MP (WOS:000287161600020) 2011; 50 YERXA, BR (WOS:A1994NN44600006) 1994; 50 Michael, JP (WOS:000244159100008) 2007; 24 Ciufolini, MA (WOS:A1996VX05500011) 1996; 118 Pansare, SV (WOS:000289361100005) 2011; 2011 Yamashita, S (WOS:000264308100010) 2009; 2009 Zeng, W (WOS:000257953600050) 2008; 73 Guimond, N (WOS:000277999700021) 2010; 132 Umeda, N (WOS:000255994700035) 2008; 47 Qi, XX (WOS:000301958500025) 2012; 48 Jiang, YJ (WOS:000301550800045) 2012; 134 Wang, KL (WOS:000250344300031) 2007; 72 Fürstner, A (WOS:000241013100010) 2006; 12 Hyster, TK (WOS:000280456100055) 2010; 132 Thomas, CJ (WOS:000220481200002) 2004; 12 Zhou, HB (WOS:000248344400044) 2007; 72 Patureau, FW (WOS:000288035300002) 2011; 50 Song, GY (WOS:000302559700014) 2012; 41 Li, B (WOS:000297541300012) 2011; 17 Simmons, E. M. (000308399500031.42) 2012; 124 Xiao, XS (WOS:000235624800020) 2006; 49 Mochida, S (WOS:000280243900035) 2010; 39 Lourdusamy, E (WOS:000283818600025) 2010; 49 Michael, JP (WOS:000232165800004) 2005; 22 Li, ZG (WOS:000172596000001) 2001 Rossiter, LM (WOS:000272462100049) 2009; 74 Wang, ZW (WOS:000274281000008) 2010; 2010 Satoh, T (WOS:000283386600001) 2010; 16 Yang, XM (WOS:000275885400011) 2010; 12 Colby, DA (WOS:000305321100005) 2012; 45 Song, GY (WOS:000283531100064) 2010; 75 Schröder, N (WOS:000304285700003) 2012; 134 Rakshit, S (WOS:000280086800026) 2010; 132 Lourdusamy, E. (000308399500031.20) 2010; 122 Pin, F (WOS:000253595100036) 2008; 73 Guimond, N (WOS:000292715500050) 2011; 133 Hyster, TK (WOS:000292964700028) 2011; 2 Babjak, M (WOS:000235280700007) 2006; 4 Du, W (WOS:000186244800001) 2003; 59 |
| References_xml | – reference: A. Camacho-Davila, J. W. Herndon, J. Org. Chem. 2006, 71, 6682-6685; – reference: C. J. Thomas, N. J. Rahier, S. M. Hecht, Bioorg. Med. Chem. 2004, 12, 1585-1604. – reference: W. Du, Tetrahedron 2003, 59, 8649-8687; – reference: G. Song, D. Chen, C.-L. Pan, R. H. Crabtree, X. Li, J. Org. Chem. 2010, 75, 7487-7490. – reference: J. P. Michael, Nat. Prod. Rep. 2005, 22, 603-626; – reference: N. Schröder, J. Wencel-Delord, F. Glorius, J. Am. Chem. Soc. 2012, 134, 8298-8301; – reference: X. Qi, Y. Jiang, C.-M. Park, Chem. Commun. 2011, 47, 7848-7850. – reference: S. Kim, Y. M. Lee, J. Lee, T. Lee, Y. Fu, Y. Song, J. Cho, D. Kim, J. Org. Chem. 2007, 72, 4886-4891; – reference: F. Pin, S. Comesse, M. Sanselme, A. Daïch, J. Org. Chem. 2008, 73, 1975-1978; – reference: For a highlight, see: F. W. Patureau, F. Glorius, Angew. Chem. 2011, 123, 2021-2023; – reference: E. Lourdusamy, L. Yao, C.-M. Park, Angew. Chem. 2010, 122, 8135-8139; – reference: J. P. 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| Snippet | Annulation: The efficient synthesis of 3‐hydroxyalkyl isoquinolones and 6‐hydroxyalkyl 2‐pyridones is enabled through the intramolecular annulation of... Annulation: The efficient synthesis of 3-hydroxyalkyl isoquinolones and 6-hydroxyalkyl 2-pyridones is enabled through the intramolecular annulation of... |
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| SubjectTerms | 2-pyridones Activation Alkaloids - chemical synthesis Alkaloids - chemistry Alkynes Alkynes - chemistry annulation Carbon - chemistry Catalysis Chemical reactions Chemistry Chemistry, Multidisciplinary Cyclization CH activation Esters Heterocyclic Compounds, 4 or More Rings - chemical synthesis Heterocyclic Compounds, 4 or More Rings - chemistry Hydrogen - chemistry Indoles - chemical synthesis Indoles - chemistry Indolizines - chemical synthesis Indolizines - chemistry Isoquinolines - chemistry isoquinolones Organic chemistry Oxidants Phenanthrenes - chemical synthesis Phenanthrenes - chemistry Phenanthrolines - chemical synthesis Phenanthrolines - chemistry Physical Sciences Pyridones - chemistry rhodium Rhodium - chemistry Science & Technology Stereoisomerism Synthesis Tolerances |
| Title | Rhodium(III)-Catalyzed Intramolecular Annulation through CH Activation: Total Synthesis of (±)-Antofine, (±)-Septicine, (±)-Tylophorine, and Rosettacin |
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