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Paper | Special issue | Vol 62, No. 1, 2004, pp.735-748
Published online, 17th November, 2003
DOI: 10.3987/COM-03-S(P)72
Microwave Assisted Pericyclic Reactions in Cascade to Construct Decalin Frameworks Possessing Quaternary Centers. Scope and Limitations

Julie A. Farand, Irina Denissova, and Louis Barriault*

*Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, K1N 6N5, Canada

Abstract

The synthesis of decalin skeletons possessing quaternary carbon centers at C9 using the tandem oxy-Cope/ene/Claisen is described. The degree of substitution at the terminal olefin plays an important role in determining the pathway of the reaction. In the case of 1,2-divinylcyclohexanol having a 1,2-disubstituted allyl ether, the corresponding decalin skeletons were obtained in good yields. In the case of trisubstituted allyl ethers, decalin products resulting from a radical 1,3-shift were isolated. The microwave irradiation of 1,2-divinylcyclohexanol propargyl ethers produced tetracyclic acetal sesquiterpenes via an oxy-Cope/ene/Claisen/5-exo dig cyclization reaction in high diastereoselectivity. The scope and limitation of the method is described.