Synthesis of Bufalitoxin and Bufotoxin

George Pettit, Yoshiaki Kamano, Pavel Drašar, Masuo Inoue, John C. Knight

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

Completion of a formal total synthetic route to the toad venom constituents bufotalin (8), cinobufagin (2a), bufalitoxin (3f), and bufotoxin (la) has been accomplished. Bufalin (3a) was employed as relay and converted to 14-dehydrobufalin 3-acetate (4). Selective oxidation of olefin 4 with a chromium trioxide-pyridine reagent afforded 16-ketone 5, which we had previously transformed to bufotalin (8) and thence to cinobufagin (2a). Condensation of bufalin (3a) with suberic anhydride followed by a mixed carbonic anhydride reaction sequence using arginine monohydrochloride yielded bufalitoxin (3f), and an analogous route from bufotalin (8) led to bufotoxin (la).

Original languageEnglish (US)
Pages (from-to)3573-3578
Number of pages6
JournalJournal of Organic Chemistry
Volume52
Issue number16
DOIs
StatePublished - Aug 1 1987

ASJC Scopus subject areas

  • Organic Chemistry

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