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

Peng Zhao; Christopher M. Beaudry

doi:10.1055/s-0034-1378713

Synlett, Inhaltsverzeichnis

Synlett 2015; 26(14): 1923-1929
DOI: 10.1055/s-0034-1378713

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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

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Abstract

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

Key words

Diels–Alder - pyrone - cyclophane - chirality - total synthesis

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Referenzen

References and Notes

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