A Synthesis of Petrofuran Based on the Enantioselective Reduction of 1-Trimethylsilyl-4-alken-1-yn-3-ones

All articles of this category 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-trimethyl-silyl-4-alken-1-yn-3-one ( 2 ) with Alpine-Borane or with BH 3 · SMe 2 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 . enantioselective reduction - oxazaborolidines - Petrosia sp. - polyacetylenes - sponge metabolites