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Total syntheses of naturally occurring seimatopolide a and its enantiomer from chiral pool starting materials using a bidirectional strategy

  • Enantioselective total syntheses of both enantiomers of the recently isolated decanolide natural product seimatopolide A are described. The C-2-symmetric building blocks (R,R)-hexa-1,5-diene-3,4-diol (derived from D-mannitol) and its enantiomer (derived from L-(+)-tartrate) serve as key starting materials, which are elaborated in a bidirectional way using a selective mono-cross-metathesis, regio- and stereoselective epoxidation, and regioselective reductive epoxide opening to furnish the first fragment. Both enantiomers of the second fragment, 3-hydroxypent-4-enoic acid, were conveniently obtained through a lipase-catalyzed kinetic resolution and merged with the first fragment via Shiina esterification. An E-selective ring-closing metathesis was used to access the 10-membered lactone. A comparison of the specific optical rotations of synthetic seimatopolides with those reported for the natural product suggests that the originally assigned (3R,6R,7R,9S)-configuration should be corrected to (3S,6S,7S,9R).

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Author:Bernd SchmidtORCiDGND, Oliver Kunz, Monib H. Petersen
ISSN:0022-3263 (print)
Parent Title (English):The journal of organic chemistry
Publisher:American Chemical Society
Place of publication:Washington
Document Type:Article
Year of first Publication:2012
Year of Completion:2012
Release Date:2017/03/26
First Page:10897
Last Page:10906
Funder:Deutsche Forschungsgemeinschaft (DFG) [Schm1095/6-2]
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert