A synthesis of petrofuran based on the enantioselective reduction of 1- trimethylsilyl-4-alken-1-yn-3-ones

Article abstract of DOI:10.1055/s-1999-6183

Highly enantioenriched 4-alken-1-yn-3-ol moiety (1), present in many bioactive acetylenic metabolites from sponges, has been efficiently obtained by reduction of the parent 1-trimethylsilyl-4-alken-1-yn-3-one (2) with Alpine-Borane or with BH₃ · SMe₂ in the presence of chiral oxazaborolidines, followed by desilylation of the resulting alcohol. This strategy has been applied to the first stereoselective synthesis of petrofuran 3.