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

Highly enantioenriched 4-alken-1-yn-3-ol moiety (1), present in many bioact ive acetylenic metabolites from sponges, has been efficiently obtained by r eduction 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, follow ed by desilylation of the resulting alcohol. This strategy has been applied to the first stereoselective synthesis of petrofuran 3.