Asymmetric and Regiospecific Synthesis of Isotopically Labelled Cyclopropane Fatty Acid (9R,10S)-Dihydrosterculic Acid: Overcoming Spontaneous Protonation During Lithium-Sulfoxide Exchange

Asymmetric and Regiospecific Synthesis of Isotopically Labelled Cyclopropane Fatty Acid (9R,10S)-Dihydrosterculic Acid: Overcoming Spontaneous Protonation During Lithium-Sulfoxide Exchange

Abstract The total synthesis of isotopically labelled (9R,10S)-dihydrosterculic acid, a usual cyclopropane fatty acid with biologically relevant toxicity upon desaturation in vivo, is reported. A diastereoselective Corey–Chaykovsky reaction was employed to form the cyclopropane ring. Rapid quenchi...

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Bibliographic Details
Main Authors:	Samuel W. J. Shields, Peter H. Buist, Jeffrey M. Manthorpe
Format:	Article
Language:	English
Published:	Georg Thieme Verlag KG 2018-04-01
Series:	SynOpen
Subjects:	lithium-sulfoxide exchange deuterium labelling asymmetric corey–chaykovsky cyclopropanation cyclopropane fatty acids mechanistic probes fatty acid desaturation
Online Access:	http://www.thieme-connect.de/DOI/DOI?10.1055/s-0036-1591976

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