Nature-Inspired Total Synthesis of (−)-Fusarisetin A
- 2 March 2012
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 134 (11), 5072-5075
- https://doi.org/10.1021/ja300807e
Abstract
A concise, protecting group-free total synthesis of (−)-fusarisetin A (1) was efficiently achieved in nine steps from commercially available (S)-(−)-citronellal. The synthetic approach was inspired by our proposed biosynthesis of 1. Key transformations of our strategy include a facile construction of the decalin moiety that is produced via a stereoselective IMDA reaction and a one-pot TEMPO-induced radical cyclization/aminolysis that forms the C ring of 1. Our route is amenable to analogue synthesis for biological evaluation.Keywords
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