Bufadienolides. 21. Synthesis of Cinobufagin from Bufotalin

George Pettit, Yoshiaki Kamano

Research output: Contribution to journalArticle

20 Scopus citations

Abstract

A synthetic method was developed for transformation of bufotalin (la) to cinobufagin (5b). The procedure was based on dehydration of bufotalin acetate (1b) to olefin 2 which upon treatment with hypobromous or hypoiodous acid afforded halohydrin 4. Treatment of halohydrin 4 with either activated alumina or pyridine yielded cinobufagin acetate (5a). Selective acid-catalyzed hydrolysis of diacetate 5a was employed to obtain cinobufagin (5b). A number of other cinobufagin derivatives were prepared including deacetylcinobufagin (5d) and the new bufadienolide 3-epicinobufagin (9a).

Original languageEnglish (US)
Pages (from-to)4040-4044
Number of pages5
JournalJournal of Organic Chemistry
Volume37
Issue number25
DOIs
StatePublished - Dec 1 1972

ASJC Scopus subject areas

  • Organic Chemistry

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