Bufadienolides. 25. Direct conversion of 14-dehydrobufalin to bufalin

Yoshiaki Kamano, George Pettit

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The easily prepared iodo- (3b), bromo- (3c), and chlorohydrin (3d) derivatives of 14-dehydrobufalin (1a), when subjected to careful hydrogenolysis using Urushibara nickel A or Raney nickel, readily yield bufalin (3a). This experimentally simple route from 14-dehydrobufalin to bufalin obviates the prior necessity of proceeding via resibufogenin (2a). In related experiments, treatment of resibufogenin (2a) with hydrogen chloride was found to yield chlorohydrin 3d, and the reverse reaction was achieved using hot α-collidine. A new procedure for selective hydrolysis of bufadienolide 3β-acetates was realized employing an acidic ion exchange resin.

Original languageEnglish (US)
Pages (from-to)2202-2204
Number of pages3
JournalJournal of Organic Chemistry
Volume38
Issue number12
StatePublished - 1973

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Bufanolides
Chlorohydrins
Nickel
Ion Exchange Resins
Hydrogenolysis
Hydrochloric Acid
Hydrolysis
Acetates
Derivatives
Experiments
bufalin
bufogenin

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Bufadienolides. 25. Direct conversion of 14-dehydrobufalin to bufalin. / Kamano, Yoshiaki; Pettit, George.

In: Journal of Organic Chemistry, Vol. 38, No. 12, 1973, p. 2202-2204.

Research output: Contribution to journalArticle

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