Preparation of Campholenal Analogues: Chirons for the Lipophilic Moiety of Sandalwood-Like Odorant Alcohols

Article abstract of DOI:10.1002/hlca.19920750507

In connection with structure-activity relationship studies, analogues of campholenal ((+)-4b), an important building block for sandalwood-like odorants, were prepared.The five-membered-ring analogues 4 were obtained by epoxidation of the corresponding α-pinene derivatives 2, followed by catalytic ZnBr2 isomerisation (Scheme 2).The six-membered-ring skeleton was obtained by ozonolysis of α-campholenyl acetate ((-)-14b), followed by intramolecular aldol condensation (Scheme 5). 13C-NMR assignments are given.