General Syntheses of 6- and 7-Carbomethoxy-trans-1-heteradecalins and 6- and 7-Carbomethoxy-trans-2-heteradecalins

Article abstract of DOI:10.1021/jo00362a012

Two routes to all of the title compounds in the oxa and aza series have been studied.The most general path, involving a cyclohexene oxide intermediate, was not successful becauase of difficulty in separating regioisomers.Allylation of 4-carbomethoxycyclohexanone (11) followed by reduction produced the required trans-disubstituted allyl alcohols, which were converted to all of the desired 6-carbomethoxy-trans-1-heteradecalins.The allyl ketones were subjected to a homologation-side chain contraction sequence to produce the 6-carbomethoxy-trans-2-heteradecalins.Allylation of 3-carbomethoxycyclohexanone (12) was not regioselective, but all four product isomers were characterized.The desired 5-carbomethoxy-2-allylcyclohexanone isomers (27 and 28) were converted to the 7-carbomethoxy-trans-decalins by similar series of reactions