A new Enantiospecific Route toward Monocarbocyclic Terpenoids: Synthesis of (-)- Caparrapi Oxide
نویسندگان
چکیده
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 l l p toluenesulphonyloxydriman-7ct-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. © 1998 Elsevier Science Ltd. All rights reserved.
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