Synthesis of 3β-Hydroxy-5α-card-20 (22)-enolide (14-Deoxy-14β-uzarigenin)
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The synthesis of 3β-hydroxy-5α-card-20 (22)-enolide (14-deoxy-14β-uzarigenin) (IX) was accomplished using 3β-acetoxy-5α, 14β, 17α-pregnan-20-one (I) derivable from △^<16>-pregnenolone acetate as the starting material. The synthesis involved an inversion of the side chain at C_<17> (I→V) by Serini-Logemann reaction, Reformatsky condensation of V with ethyl bromoacetate, selenium dioxide oxidation to the butenolide (VIII) followed by saponification with acid. Isomerization of IX to 3β-hydroxy-5α, 17α-card-20 (22)-enolide (14-deoxy-14β, 17α-uzarigenin) (XI) was described, which was also prepared from I.
- 公益社団法人日本薬学会の論文
- 1968-11-25
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