Abstract
The chemical composition of a fossil resin from a Miocene outcrop in Brunei, South East Asia, is compared with its extant counterpart dammar, obtained from trees of the family Dipterocarpaceae, to establish the nature of the precursor of bicadinanes. The alcohol soluble fractions of the resins consist of functionalised triterpenoids and a small amount of sesquiterpenoids. None of the compounds present in this fraction bears any structural relation to bicadinanes. The alcohol insoluble fractions of the resins consist of a polymer based on cadinene. A structure for this polymer is proposed. Heating the polymer in dammar resin resulted in the formation of monomeric, dimeric, and trimeric cadinenes. It is thought that the naturally occurring bicadinanes result from dimeric cadinenes upon cyclisation.
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