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3-Deoxy-3-oxoingenol (3) was prepared from ingenol-5,20-acetonide (25) by oxidation and subsequent removal of the acetonide. 3 was acylated to give homologous 5,20-diacylates 5-9. From these the 5-monoacylates 14, 15 and 17 were obtained in only moderate yields. Therefore the 20-silyl ether 10 (prepared from 3) was acylated. After smooth removal of the silyl ether the homologous 5-acylates 16. 18 and 19 resulted in good yield. The 5,20-dibutyrate 6 and all 5-acylates prepared (14-19) showed no irritant activity on the mouse ear. The 3-oxo-5-acylates 14-19 could not be reduced to give ingenol-5-acylates (24). Therefore various ingenol derivatives, 29-32, with suitable protected hydroxyl functions as well as the corresponding 5-clecanoates 35-38 were synthesized. The protecting groups of the derivatives 35-38 could however not be cleaved off to yield ingenol-5- decanoate (24)

On the Chemistry of Ingenol, III [1] Synthesis of 3-Deoxy-3-oxoingenol, Some 5-Esters and of Ethers and Acetals of Ingenol