Synthesis of bicyclic homochiral dienes by allylic rearrangement of cyclohexenols - Suitable building blocks for the synthesis of nagilactones

Article abstract of DOI:10.1002/jlac.199719970214

A very short and straightforward synthesis towards highly functionalized dienes is described. The homochiral starting material, unsaturated β-oxo ester 2, can be prepared by enzyme-catalyzed saponification. The utility of the dienes has been demonstrated in a cycloaddition with N-phenyltriazolidinone as the dienophile. The Diels-Alder reaction is highly diastereoselective, yielding only one diastereomer. VCH Verlagsgesellschaft mbH, 1997.