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

Louis Barriault; Irina Denissova; Nathalie Goulet

doi:10.1055/s-0031-1291144

Synthesis, Table of Contents

Synthesis 2012; 44(12): 1833-1840
DOI: 10.1055/s-0031-1291144

special topic

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

Authors

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

Abstract

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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.

Key words

oxy-Cope/ene/Claisen - domino - sigmatropic - diastereoselectivity - macrocycle

Full Text

References

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Supplementary Material

Supporting Information (PDF)