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

David M Hodgson; Eric P A Talbot; Barry P Clark

doi:10.1021/ol202425e

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

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

Authors

David M Hodgson¹, Eric P A Talbot, Barry P Clark

Affiliation

¹ Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. david.hodgson@chem.ox.ac.uk

PMID: 21981361
DOI: 10.1021/ol202425e

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Cyclization
Ketones / chemistry*
Lactones / chemical synthesis*
Molecular Structure
Sesquiterpenes / chemical synthesis*
Stereoisomerism

Substances

Ketones
Lactones
Sesquiterpenes
anthecotulide