The reactions of 5α-allyl-1,1-ethylenedioxy-5β,9β-dimethyl-trans-decalin-6-one, a potential intermediate in the synthesis of friedolabdanes

Abstract

5α-Allyl-1,1-ethylenedioxy-5β,9β-dimethyl-trans-decalin-6-one (8) has been prepared. In connection with its potential use for the synthesis of friedolabdanes a number of reactions of this compound and its derivatives have been studied. These include epoxidation, ozonolysis, and the attempted hydration of the double bond via hydroboration. The products of these reactions have indicated very substantial participation of the functional group at C-6 in the reactions of the double bond. In particular a novel reaction occurred on hydroboration involving carbon–carbon bond formation between the ethylenic and carbonyl groups.