Abstract
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.
© 1946 – 2014: Verlag der Zeitschrift für Naturforschung
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.