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A Concise Approach to Vinigrol


  • 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.


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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.