Bufadienolides. VII. Ring-Opening Reaction of 14,15-α, β-Epoxides with Hydroiodic Acid
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概要
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Resibufogenin (IX), which is 14β, 15β-epoxy compound in bufadienolides, occurs in nature, but the corresponding 14α, 15α-epoxy compound is unknown. In order to examine the ring-opening reaction of 14,15-epoxy function with hydroiodic acid, 14α, 15α-epoxy-3β-hydroxy-5β-bufa-20,22-dienolide (VI) and its 3-acetate (VII) were synthesized (Chart 1). Reaction of 14β, 15β-epoxy compound (IX) or 14α, 15α-epoxy compound (VI) with hydroiodic acid gave Δ^<14>-anhydrobufalin (II), which was a normal reduced product, 14α-artebufogenin (XI), and 14β-artebufogenin (XIII), respectively. A similar reaction of two acetates (X or VII) gave the corresponding acetates, IV, XII and XIV, respectively (Chart 2). The formation of 14α- and 14β-artebufogenin indicates that the acid-catalyzed ring-opening reaction occurred at a time. Based on these results, reaction of 5,6-epoxy function was reexamined. As was excepted, reaction of 5β, 6β-epoxy compound (XV) or 5α, 6α-epoxy compound (XVI) afforded 3β-acetoxy-5,6β-dihydroxy-5α-cholestane (XIX), besides cholesteryl acetate (XVII) and cholesterol (XVIII).
- 公益社団法人日本薬学会の論文
- 1969-08-25
著者
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釜野 徳明
Cencer Reseach Institute And Department Of Chemistry Arizona State University
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釜野 徳明
Research Laboratories Taisho Pharmaceutical Co. Ltd.
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