Synthesis
DOI: 10.1055/s-0036-1588557
paper
© Georg Thieme Verlag Stuttgart · New York

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

Papiya Dey, Sucheta Chatterjee, Sunita S. Gamre, Subrata Chattopadhyay, Anubha Sharma*
  • Bio-Organic Division, Bhabha Atomic Research Centre, Mumbai 400 085, India   Email: anubhas@barc.gov.in
Further Information

Publication History

Received: 27 July 2017

Accepted after revision: 29 July 2017

Publication Date:
29 August 2017 (eFirst)

§ 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.

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