Abstract
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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