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Org Lett. 2011 Nov 4;13(21):5751-3. doi: 10.1021/ol202425e. Epub 2011 Oct 7.

Catalytic asymmetric synthesis of (+)-anthecotulide using enyne and Meyer-Schuster rearrangements.

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  • 1Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK.


The bioactive sesquiterpene lactone (+)-anthecotulide (1) is synthesized for the first time, in a six-step sequence devoid of protecting groups. The key transformations are a novel Rh(I)-catalyzed asymmetric enyne rearrangement of a terminal alkynyl ester (4), to form the α-methylene-γ-butyrolactone core, and a final-step mild Au(I)-catalyzed Meyer-Schuster rearrangement.

© 2011 American Chemical Society

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