The transformation of 11-deoxojervine into 18-functional C-nor-D-homosteroids.
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Deoxojervine, a <I>C</I>-nor-<I>D</I>-homosteroidal alkaloid, has been transformed into 17β-acetyl-12α-etiojervan-3β-ol acetate in 3 steps. Treatment with base gave the 17α-epimer. Reduction of the 17β-isomer with NaBH<SUB>4</SUB> afforded 17β-ethyl-12α-etiojervane-3β,20β-diol 3-acetate as a single product whereas reduction of the 17α-isomer afforded 17β-ethyl-12α-etiojervane-3β,20β-diol 3-acetate and the 20α isomer in an approximate 1 : 1 ratio. Irradiation of 17β-ethyl-12α-etiojervane-3β,20β-diol 3-acetate in cyclohexane in the presence of lead tetraacetate and iodine afforded a C-18 functional <I>C</I>-nor-<I>D</I>-homosteroid as a 18,20-epoxide which was oxidized to the corresponding γ-lactone with chromium trioxide. A mixture of the 17α-ethyl-12α-etiojervane-3β,20α-diol 3-acetate and its 20β isomer in contrast gave no 18-functional compounds upon irradiation under similar conditions.
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