Stereoselective Total Synthesis of (6S)-5,6-Dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one from L-Malic Acid

Abstract

A stereoselective total synthesis of an antiproliferative and antifungal natural product, (6 S)-5,6-dihydro-6-[(2 R)-2-hydroxy-6-phenylhexyl]-2 H-pyran-2-one has been accomplished using the Barbier allylation, LiAlH4/LiI mediated syn-stereoselective reduction and olefin ring-closing metathesis (RCM) as the key steps. L-Malic acid was used as a chiral precursor for the construction of syn-1,3-diol moiety of the molecule.