Issue 0, 1973

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.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1973, 853-858

The pimarane → cassane rearrangement. Synthesis of a potential intermediate from isopimaric acid

J. P. Johnston and K. H. Overton, J. Chem. Soc., Perkin Trans. 1, 1973, 853 DOI: 10.1039/P19730000853

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