An Enantioselective Synthesis of (5S,6R,11S,14R)-Acremodiol
Received: 27 July 2017
Accepted after revision: 29 July 2017
29 August 2017 (eFirst)
§ Equal contributions.
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.