A Concise Approach to Vinigrol†
Thomas J. Maimone
Department of Chemistry, The Scripps Research Institute, 10650 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-7375
Search for more papers by this authorAna-Florina Voica
Department of Chemistry, The Scripps Research Institute, 10650 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-7375
Search for more papers by this authorPhil S. Baran Prof.
Department of Chemistry, The Scripps Research Institute, 10650 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-7375
Search for more papers by this authorThomas J. Maimone
Department of Chemistry, The Scripps Research Institute, 10650 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-7375
Search for more papers by this authorAna-Florina Voica
Department of Chemistry, The Scripps Research Institute, 10650 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-7375
Search for more papers by this authorPhil S. Baran Prof.
Department of Chemistry, The Scripps Research Institute, 10650 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-7375
Search for more papers by this authorWe 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.
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.
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