Chemistry of Natural Compounds p. 142 - 145 (1981)
Update date:2022-08-04
Topics:
Kamernitskii, A. V.
Krivoruchko, V. A.
Reshetova, I. G.
Chernoburova, E. I.
The synthesis of the Δ17(20)-16α analog of natural chiogralactone is described.Attempts to introduce a 6-oxo group directly into the δ-lactone proved unsuccessful, since the first stage - saponification - took place with the formation of three products: the 3-hydroxy-δ-lactone, the 3-hydroxy-Δ20(22)-lactone, and the 15,17(20)-dienoic acid.The synthesis of the desired compound was effected from the ethyl ester of the 5,16-dienoic acid by the scheme 3-acetate->3-tosylate->6-hydroxy-3α,5α-cyclosteroid->6-oxo-3α,5α-cyclosteroid->6-oxo-5αH-δ-lactone.It has been shown that the cyclopropane ring in the 3α,5α-cyclosteroid δ-lactone is extremely stable under the conditions of acid treatments.
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