A key intermediate for the chiral synthesis of elemanoids. Synthesis of (+)-.beta.-elemenone
- Publikations-Art
- Zeitschriftenbeitrag
- Autoren
- Kato, M.; Vogler, B.; Tooyama, Y.; Yoshikoshi, A.
- Erscheinungsjahr
- 1990
- Veröffentlicht in
- Chem. Lett.
- Band/Volume
- 1/
- Seite (von - bis)
- 151-4
(1R,5S)-3-Phenylsulfenyl-6,6-dimethylbicyclo[3.1.1]heptanone obtained from (+)-nopinone was transformed into (1R,4S,5S)-4-methyl-4-vinylbicyclo[3.1.1]heptan-2-one, whose cyclobutane ring was cleaved with BF3.EtO2(OAc)2 in Ac2O to provide (4S,5S)-1-acetoxy- 4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene (I), the key intermediate, in a highly regio- and stereoselective manner. Regioselective introduction of a three-carbon unit to I with acetone followed by dehydration yielded (+)-.beta.-elemenone (II).