M. Kato, B. Vogler, Y. Tooyama
1990
Citations
0
Influential Citations
3
Citations
Journal
Chemistry Letters
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–Zn(OAc)2 in acetic anhydride to provide (4S,5S)-1-acetoxy-4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene (5), the key intermediate, in a highly regio- and stereoselective manner. Regioselective introduction of a three-carbon unit to 5 with acetone followed by dehydration yielded (+)-β-elemenone.