Synthetic Studies on the Ochtodane Type Terpenes I. Stereoselective Construction of the Ochtodane Skeleton from Myrcene

Y Masaki, K Hashimoto, K Sakuma, K Kaji

Index: Masaki; Hashimoto; Sakuma; Kaji Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 12 p. 3466 - 3475

Full Text: HTML

Citation Number: 6

Abstract

The ochtodane skeleton, the Carbon framework of 1, 1-dimethyl-3-ethylcyclohexane (1) was constructed highly stereoselectively by the acid-catalyzed (SnCl 4 or CF 3 CO 2 H) cyclization of the terminally functionalized myrcene derivatives, the benzenesulfenyl chloride adduct (7), the terminal β-hydroxy sulfide (8) derived from 7, and myrcene 6, 7-epoxide (10). The stereoselectivity of the 3-exo-double bond in 1 formed concomitantly in the cyclization ...