Three new oxygenated cadinanes from Baccharis species

Article abstract of DOI:10.1016/0031-9422(95)00977-9

Synthesis of several (±)-[4S-(4β,4αβ,8aα)]-1,6-dimethyl-4- ([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-methyl-ethyl)-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- methyletyl-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.