Total Syntheses of Aflatoxins M1 and G1 and an Improved Synthesis of Anatoxin B1

G. Biichi, Steven M. Weinreb

Research output: Contribution to journalArticle

93 Citations (Scopus)

Abstract

Starting with 4,6-dihydroxybenzofuran-3[2H]-one (4) the tricyclic phenol 29 was prepared in 11 steps. Condensation of 29 with the vinyl bromide 33 in methylene chloride solution in the presence of zinc carbonate produced racemic milk toxin (3). This new coumarin synthesis seems to be generally applicable and particularly useful whenever acid-sensitive phenols forbid the practice of the classical Pechmann synthesis. An improved synthesis of aflatoxin B1 (1) resulted when the new method was applied to the phenol 42. Finally aflatoxin G1 (2) was prepared analogously from the phenol 42 and the bromo lactone 47.

Original languageEnglish (US)
Pages (from-to)746-752
Number of pages7
JournalJournal of the American Chemical Society
Volume93
Issue number3
DOIs
StatePublished - Feb 1 1971

Fingerprint

Aflatoxin M1
Aflatoxins
Phenol
Phenols
Aflatoxin B1
Methylene Chloride
Lactones
Condensation
Dichloromethane
Milk
Carbonates
Acids
Zinc
aflatoxin G1

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

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Total Syntheses of Aflatoxins M1 and G1 and an Improved Synthesis of Anatoxin B1. / Biichi, G.; Weinreb, Steven M.

In: Journal of the American Chemical Society, Vol. 93, No. 3, 01.02.1971, p. 746-752.

Research output: Contribution to journalArticle

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