Tobacco chemistry. 65. Two new 7,8-epoxycembranoids from tobacco.

Abstract

Two new diterpenoids have been isolated from tobacco. They have been identified as the (1S,2E,4S,6R,7R,8R,11E)- and (1S,2E,4S,6R,7S,8S,11E)-7,8-epoxy-2,11-cembradiene-4,6-diols 1 and 2 by synthesis and X-ray analysis. The conformation about the 5,6 bond in some 7,8-epoxycembranoids is discussed, as is the biogenesis of the two new compounds.