Bufadienolides. 17. Synthesis of 14α- and 14β-Artebufogenin
- 15 June 1973
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 51 (12) , 1973-1976
- https://doi.org/10.1139/v73-295
Abstract
Treatment of resibufogenin (1a) or its acetate (1b) with perchloric acid or hydrochloric acid gave 14α-and 14β-artebufogenin (5a and 6a, or 5b and 6b), in addition to 15α-hydroxy-bufalin (4a or b). Reaction of epoxide 1b with chloranil or boron trifluoride etherate easily afforded 14α- and 14β-artebufogenin acetate (5b and 6b) in good yields. Analogous reaction of the isomeric 3β-hydroxy-14α,15α-epoxide 3a with perchloric acid, hydrochloric acid, or sulfuric acid again led to 14α- and 14β-artebufogenin (5a and 6a) and the 14β,15α-dihydroxy-derivative 4a, Similar reaction with periodic acid gave 6a and 4a.Keywords
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