Oxidation Products of Totara-8,11,13-trien-13-ol Derivatives

Abstract

Reaction of 7-oxototara-8,11,13-trien-13-yl acetate (3) with acetic anhydride-perchloric acid affords the γ-pyrone (8) in addition to the previously reported acetyl derivative (4). Baeyer–Villiger oxidations of the ketones (3) or (5) have given starting material or complex mixtures, but the ϵ-lactone (9) and the rearranged product (11) were isolated from two experiments with (3). Oxidation of 13-methoxytotara-8,11,13-triene (2) with Jones reagent gives the 7-oxo derivative (5) and a low yield of a ring B opened substituted p-benzoquinone (13). Pathways to (11) and (13) are proposed.