(R)-Recifeiolide, a naturally occurring macrolactone, was synthesized in optically pure form by the aid of biocatalysts. Lipase-catalyzed lactonization of the racemic precursor afforded the desired compound with a concomitant kinetic resolution. The optically active acyclic precursor could be synthesized by the reduction of corresponding ketone with Pichia farinosa IAM 4682. The yeast reduction proceeded with the anti-Prelog rule, selecting si-face attack on the carbonyl group to give (R)-alcohol with > 95% e.e.
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