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A new nine steps synthesis of the 21-acetate 6α-fluoro 16α-hydroxy substance S 16α, 17α-acetonide (XVII) is described. This compound is a key intermediate in the synthesis of the high anti-inflammatory hormone (XIX).

The diacetylenic steroids (VI), (VII) and (X) have been prepared by the cupric acetate — pyridine method. The “bis-norlutine” (VI) has been partially hydrogenated to the corresponding “diene” (VIII) and the “bis-acetate” (X a) has been converted to “bis-ethisterone” (VII).

The conversion of 19-nortestosterone acetate into 19-norandrosta-4,7-diene-3,17-dione (X) is described. The latter compound is transformed directly into equilin by a microbiological dehydrogenation process with Corynebacterium simplex , thus representing the first synthesis of this important female sex hormone. Alternate attempts to synthesise equilin are discussed.