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Synthesis 2017; 49(23): 5231-5237
DOI: 10.1055/s-0036-1588557
DOI: 10.1055/s-0036-1588557
paper
An Enantioselective Synthesis of (5S,6R,11S,14R)-Acremodiol
Further Information
Publication History
Received: 27 July 2017
Accepted after revision: 29 July 2017
Publication Date:
29 August 2017 (online)
§ 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 transesterificationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588557.
- Supporting Information
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