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

Internet

http://www.thieme-connect.de/DOI/DOI?10.1055/s-0036-1591976

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