Synthesis of the tricyclic core of labiatin A and australin A

Clark, J.S. , Vignard, D. and Parkin, A. (2011) Synthesis of the tricyclic core of labiatin A and australin A. Organic Letters, 13(15), pp. 3980-3983. (doi:10.1021/ol201498g)

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Publisher's URL: http://dx.doi.org/10.1021/ol201498g

Abstract

A concise synthesis of the tricyclic core of the marine diterpene natural products labiatin A and australin A has been accomplished. The key ring-forming transformation is a cascade reaction comprising generation of a copper carbenoid from a diazo ketone, intramolecular reaction of the carbenoid with a cyclic ether, and rearrangement of the resulting free oxonium ylide or its metal-bound equivalent with ring expansion of the original cyclic ether.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Clark, Professor Stephen
Authors: Clark, J.S., Vignard, D., and Parkin, A.
Subjects:Q Science > QD Chemistry
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Organic Letters
ISSN:1523-7060
ISSN (Online):1523-7052
Published Online:06 July 2011

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