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Preparation and purification of 3-acylates of ingenol (1a) structurally related to naturally occuring, irritant and cocarcinogenic principles are described. It is shown that 3-acylates partly rearrange to corresponding 5-acylates when they are chromatographecl. From the 3-acylates or from ingenol (1a) a mixed and a symmetric ingenol-3,20-diacylate is synthesized respectively. Ingenol-5,20-acetonide (2a) is rearranged to its ⊿ 7.8 -isomer 3b. Starting with 3b ⊿ 7.8 -isoingenol (3a) and the 3-tetradecanoate of ⊿ 7.8 -isoingenol (3d) are prepared. Most of the ingenol derivatives prepared are tested for their irritant activity on the mouse ear.

zeitschrift für naturforschung b

Zur Chemie des Ingenols, II [1] Ester des Ingenols und des ⊿ 7.8  -Isoingenols / On the Chemistry of Ingenol, II [1] Esters of Ingenol and ⊿ 7.8  -Isoingenol