Enantioselective Synthesis of (+)-(2R,3S,6R)-Decarestrictine L

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A convergent enantioselective synthesis of (+)-(2R,3S,6R)-decarestrictine L (1), a natural inhibitor of cholesterol biosynthesis, is described from commercially available (S)-malic acid and (R)-isobutyl lactate. The third chiral center was created by stereoselective reduction of a chiral α-hydroxy ketone, and an intramolecular SN2-type reaction allowed the stereocontrolled formation of the tetrahydropyranyl ring.