A key intermediate for the chiral synthesis of elemanoids. Synthesis of (+)-.beta.-elemenone

Publication Type: Journal contribution
Authors: Kato, M.; Vogler, B.; Tooyama, Y.; Yoshikoshi, A.
Year of publication: 1990
Published in: Chem. Lett.
Band/Volume: 1/
Page (from - to): 151-4

Abstract

(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).

Involved institutions

Institute of Chemistry
Bioorganic Chemistry