Aspects of the chemistry of the hexahydroisochromanone from the carvenone–benzaldehyde condensation

Abstract

A scheme for the mechanism of formation of the title compound is described and supported by deuteriation studies. The various courses of reduction of the title compound are described. Opening of the heterocyclic ring during attempted zinc–methanol reduction is shown to be due to formation of ‘zinc methoxide’ in the reaction. The courses of bromination and reduction of 4,4,7-trimethyl-1,3-diphenyl-5,6,7,8-tetrahydroisochroman-8-one are outlined, and structures are assigned to the products.