Structure-activity Relations of Polyfunctional Diterpenes of the Daphnane Type. I. Revised Structure For Resiniferatoxin and Structure-activity Relations of Resini-feronol and Some of its Esters

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Abstract
Base-catalyzed transesterifications of resiniferatoxin yielded 9,13,14-o-phenylacetate (3) and (4-hydroxy-3-methoxyphenyl)acetic acid methyl ester (2). Reesterification of 3 with homovanillic acid showed that the previously proposed structure for resiniferatoxin had to be revised to resiniferonol-9,13,14-o-phenylacetate-20-(4-hydroxy-3-methoxyphenyl)acetate (1). From 3 different 20-esters (1, 4-9) were prepared. The o-phenylacetate 3 was cleaved by acidic hydrolysis to yield the 14-phenylacetate 10. Subsequent alkaline transesterifications of 10 yielded the parent alcohol resiniferonol (11). Starting from 11, the 14,20-diesters 12 and 15 and the 9,13,14-o-esters 13, 14, 16, 17 and 18 were obtained. All esters were tested for irritant activity on the mouse ear. Some aspects of structure-activity relations of irritancy of resiniferonol esters were established and discussed.

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