Synthesis 2012; 44(12): 1833-1840
DOI: 10.1055/s-0031-1291144
special topic
© Georg Thieme Verlag Stuttgart · New York

Mechanistic Investigation of the Domino Oxy-Cope/Ene/Claisen Reaction and Its Application to the Synthesis of Desdimethyl Ambliol B

Louis Barriault*
Centre for Catalysis Research and Innovation, University of Ottawa, Department of Chemistry, 10 Marie Curie, Ottawa, Ontario, K1N 6N5, Canada, Fax: +1(613)5625170   Email: lbarriau@uottawa.ca
,
Irina Denissova
Centre for Catalysis Research and Innovation, University of Ottawa, Department of Chemistry, 10 Marie Curie, Ottawa, Ontario, K1N 6N5, Canada, Fax: +1(613)5625170   Email: lbarriau@uottawa.ca
,
Nathalie Goulet
Centre for Catalysis Research and Innovation, University of Ottawa, Department of Chemistry, 10 Marie Curie, Ottawa, Ontario, K1N 6N5, Canada, Fax: +1(613)5625170   Email: lbarriau@uottawa.ca
› Author Affiliations
Further Information

Publication History

Received: 20 March 2012

Accepted: 22 March 2012

Publication Date:
01 June 2012 (eFirst)

Abstract

We report an efficient and highly diastereoselective oxy-Cope/ene/Claisen reaction for the synthesis of decalin frameworks possessing four contiguous stereogenic centers. A detailed mechanistic investigation and its application to a short and protecting group free synthesis of desdimethyl ambliol B are presented.

Supporting Information

 
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