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.
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