Three new oxygenated cadinanes from Baccharis species

Abstract

Synthesis of several (±)-[4S-(4β,4aβ,8aα)]-1,6-dimethyl-4-(1 methylethyl)-1,2,3,4,5,8,8a-octahydro-1-naphthalenol derivatives (cadinanol derivatives) provided the necessary evidence for the identification of three novel cadinane derivatives [(±)-[1S-(1β, 4β, 4aβ, 8aα)]-1,6-dimethyl-4-(1-methylethyl)-1,2,3,4,4a,5,8,8a-octahydro-1-naphthalenol 11a, (±)-[1S-(1β, 4β, 4aβ, 4aβ, 6α, 7α, 8aα)]-6, 7-epoxide-1,6-dimethyl-4-(1-methylethyl)-1,2,3,4,4a,5,6,7,8,8a-decahydro-1- naphthalenol 14 and (±)-[1S-(1β,4β,4aβ,6β,8aα)]-1,6-dimethyl-4-(1-methylethyl-1,2,3,4,4a,5,6,7,8,8a-decahydro-1,6-naphthalenediol 15] detected, in the essential oils of, B. platipoda. Compound 14 was also detected in B. tridentata. The synthetic compounds were characterized by one and two dimensional 1H and 13C NMR. The identification was obtained by coinjection of the oils with the synthetic standards and fragmentation pattern comparison.