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BY-NC-ND 3.0 license Open Access Published by De Gruyter June 2, 2014

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

  • Bernd Sorg and Erich Hecker

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.

Received: 1982-2-3
Published Online: 2014-6-2
Published in Print: 1982-6-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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