An Enantioselective Synthesis of (5S,6R,11S,14R)-Acremodiol

^§ Equal contributions.

Abstract

An expeditious synthesis of the (5S,6R,11S,14R)-isomer of acremodiol was developed via a convergent route. One of the required building blocks was synthesized earlier via two sequential lipase-catalyzed secondary carbinol acetylations. The other unit was derived from (R)-2,3-cyclohexylideneglyceraldehyde as a chiral template. The bismacrolide skeleton was constructed by an intermolecular esterification reaction under Mitsunobu conditions followed by a ring-closing metathesis­ of the resultant α,ω-dialkenoic ester.

Keywords

asymmetric synthesis - (R)-2,3-cyclohexylideneglyceraldehyde - macrodiolide - ring-closing metathesis - lipase-catalyzed trans­esterification

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