Bufadienolides. 14. Synthesis of bufotalien, 15α-hydroxybufalin, and resibufogenin

George Pettit, Yoshiaki Kamano, Fred Bruschweiler, Peter Brown

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Conversion of 14-dehydrobufalin (2a) to bufotalien (4a) was accomplished. Peracid oxidation of 3β-acetoxy-14-dehydrobufalin (2b) was employed to obtain 14α,15α-epoxide 5b. Sulfuric aeid catalyzed opening of epoxide 5b was used to complete a route to 15α-hydroxybufalin (6b). Treatment of diol 6b with methanesulfonyl chloride led to a new synthesis of 3β-acetoxyresibufogenin (3b). Conversion of 14-dehydrobufalin to the halohydrins represented by structures 6d-g followed by treatment with basic alumina or hot pyridine afforded resibufogenin in good yield. The epoxide formation catalyzed by alumina was also shown to yield 14α-artebufogenin (8b).

Original languageEnglish (US)
Pages (from-to)3736-3739
Number of pages4
JournalJournal of Organic Chemistry
Volume36
Issue number24
StatePublished - 1971

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Bufanolides
Epoxy Compounds
Aluminum Oxide
Oxidation
bufogenin

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Bufadienolides. 14. Synthesis of bufotalien, 15α-hydroxybufalin, and resibufogenin. / Pettit, George; Kamano, Yoshiaki; Bruschweiler, Fred; Brown, Peter.

In: Journal of Organic Chemistry, Vol. 36, No. 24, 1971, p. 3736-3739.

Research output: Contribution to journalArticle

Pettit, G, Kamano, Y, Bruschweiler, F & Brown, P 1971, 'Bufadienolides. 14. Synthesis of bufotalien, 15α-hydroxybufalin, and resibufogenin', Journal of Organic Chemistry, vol. 36, no. 24, pp. 3736-3739.
Pettit, George ; Kamano, Yoshiaki ; Bruschweiler, Fred ; Brown, Peter. / Bufadienolides. 14. Synthesis of bufotalien, 15α-hydroxybufalin, and resibufogenin. In: Journal of Organic Chemistry. 1971 ; Vol. 36, No. 24. pp. 3736-3739.
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