Nature-inspired total synthesis of (-)-fusarisetin A.

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.

SUBMITTER: Xu J 

PROVIDER: S-EPMC3310296 | biostudies-literature | 2012 Mar

REPOSITORIES: biostudies-literature