A new enantiospecific route toward monocarbocyclic terpenoids: Synthesis of (-)- caparrapi oxide

Article abstract of DOI:10.1016/S0040-4039(98)02119-4

A new and efficient strategy is described for carrying out the enantiospecific synthesis of monocarbocyclic terpenoids from (-)-sclareol (1). The key steps are the Grob scission of 11-p-toluenesulphonyloxydriman- 7α-ol (2) to give the tobacco seco-sesquiterpene 3 and the Baeyer-Villiger oxidation of 4-[(1'S, 2'S)-2'-formyl-2',6',6'-trimethylcyclohexyl]-2-butanone (4), derived from 3. The first enantiospecific synthesis of (-)-caparrapi oxide (8) based on this methodology is reported.