Reactions with alpha,beta-Unsaturated Nitrile Oxides. Synthetic Studies in the Terpene Field. Synthesis of Tagetones, Ocimenones, Deodarone, and Atlantone.

Abstract
The generation and 1,3-dipolar cycloaddition of .alpha.,.beta.-unsaturated nitrile oxides are described. Selective reductive cleavage of the isoxazoline ring was achieved. Subsequent elimination of water leads to the 1,4-dien-3-one system. The formation of tetrahydro-.gamma.-pyrones is observed. The reactions were applied to the synthesis of tagetones, ocimenones, deodarone and atlantone.