The pimarane → cassane rearrangement. Synthesis of a potential intermediate from isopimaric acid
Abstract
The unstable cisoid enone diester dimethyl 7-oxoisopimar-8(14)ene-16,18-dioate (27), a potential intermediate for the pimarane → cassane rearrangement, has been synthesised regiospecifically from isopimara-7,15-dien-18-oic acid (isopimaric acid)(11)via the keto-lactone 18-methoxycarbonyl-7-oxo-18-norisopimaran-16,8α-olactone (25). Several unsuccessful attempts to induce the rearrangement with derivatives of the enone (27) are described.