A Concise Approach to Vinigrol
2008; Wiley; Volume: 47; Issue: 16 Linguagem: Inglês
10.1002/anie.200800167
ISSN1521-3773
AutoresThomas J. Maimone, A.-F. Voica, Phil S. Baran,
Tópico(s)Microbial Natural Products and Biosynthesis
ResumoAngewandte Chemie International EditionVolume 47, Issue 16 p. 3054-3056 Communication A Concise Approach to Vinigrol† Thomas J. Maimone, Thomas J. Maimone Department of Chemistry, The Scripps Research Institute, 10650 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-7375Search for more papers by this authorAna-Florina Voica, Ana-Florina Voica Department of Chemistry, The Scripps Research Institute, 10650 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-7375Search for more papers by this authorPhil S. Baran Prof., Phil S. Baran Prof. [email protected] Department of Chemistry, The Scripps Research Institute, 10650 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-7375Search for more papers by this author Thomas J. Maimone, Thomas J. Maimone Department of Chemistry, The Scripps Research Institute, 10650 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-7375Search for more papers by this authorAna-Florina Voica, Ana-Florina Voica Department of Chemistry, The Scripps Research Institute, 10650 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-7375Search for more papers by this authorPhil S. Baran Prof., Phil S. Baran Prof. [email protected] Department of Chemistry, The Scripps Research Institute, 10650 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-7375Search for more papers by this author First published: 01 April 2008 https://doi.org/10.1002/anie.200800167Citations: 63 † We thank Dr. D.-H. Huang and Dr. L. Pasternack for NMR spectroscopic assistance, Dr. G. Siuzdak for mass spectrometric and Dr. Arnold Rheingold (UCSD) for X-ray crystallographic assistance. Financial support for this work was provided by Bristol-Myers Squibb (predoctoral fellowship to T. J. M.), Merck, and Roche. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Short and sweet: A simple and practical route to the unusual tricyclic ring system found in the biologically active diterpene vinigrol is described. A remarkable proximity-induced intramolecular cycloaddition and mild Grob fragmentation allow rapid construction of the core ring system in less than 10 steps and with a minimal reliance on protecting groups. Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2008/z800167_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1I. Uchida, T. Ando, N. Fukami, K. Yoshida, M. Hashimoto, T. Tada, S. Koda, Y. Morimoto, J. Org. Chem. 1987, 52, 5292–5293. 2 2aT. Ando, Y. Tsurumi, N. Ohata, I. Uchida, K. Yoshida, M. Okuhara, J. Antibiot. 1988, 41, 25–30; 2bT. Ando, K. Yoshida, M. Okuhara, J. Antibiot. 1988, 41, 31–35; 2cD. B. Norris, P. Depledge, A. P. Jackson, PCT Int. Appl. WO 9107 953, 1991; 2dH. Nakajima, N. Yamamoto, T. Kaizu, T. Kino (Jpn. Kokai Tokkyo Koho), JP 07-206668, 1995. 3Studies toward vinigrol: 3aL. A. Paquette, R. Guevel, S. Sakamoto, I. H. Kim, J. Crawford, J. Org. 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These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. Citing Literature Volume47, Issue16April 7, 2008Pages 3054-3056 ReferencesRelatedInformation
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