Synlett 2015; 26(14): 1923-1929
DOI: 10.1055/s-0034-1378713
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© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of (+)-Cavicularin: The Pyrone Diels–Alder Reaction in Enantioselective Cyclophane Synthesis

Peng Zhao
Department of Chemsitry, Oregon State University, Corvallis, OR 97331, USA   Email: christopher.beaudry@oregonstate.edu
,
Christopher M. Beaudry*
Department of Chemsitry, Oregon State University, Corvallis, OR 97331, USA   Email: christopher.beaudry@oregonstate.edu
› Author Affiliations
Further Information

Publication History

Received: 08 April 2015

Accepted after revision: 30 April 2015

Publication Date:
24 June 2015 (online)

We dedicate this paper to Prof. Kenneth W. Hedberg on the occasion of his 95th birthday.

Abstract

A pyrone Diels–Alder strategy was developed for the synthesis of the cyclophane natural product, cavicularin. The strategy uses a vinyl sulfone as an alkyne equivalent dienophile. An enantioselective variant delivered (+)-cavicularin.

 
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