Quinone approaches toward the synthesis of aflatoxin B(2)

W E Noland; B L Kedrowski

doi:10.1021/ol006014r

Quinone approaches toward the synthesis of aflatoxin B(2)

Org Lett. 2000 Jul 13;2(14):2109-11. doi: 10.1021/ol006014r.

Authors

W E Noland¹, B L Kedrowski

Affiliation

¹ Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.

PMID: 10891242
DOI: 10.1021/ol006014r

Abstract

[reaction: see text] Quinones bearing electron-withdrawing groups can serve as useful precursors to furobenzofuran ring systems through their reaction with 2,3-dihydrofuran. Formal racemic and stereoselective syntheses of the fungal metabolite aflatoxin B(2) are described that utilize this approach to construct the tricyclic ABC-ring core of the molecule.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aflatoxins / chemical synthesis*
Aspergillus / chemistry
Chelating Agents
Mycotoxins / chemical synthesis*
Oxidants
Quinones / chemistry*
Stereoisomerism

Substances

Aflatoxins
Chelating Agents
Mycotoxins
Oxidants
Quinones
aflatoxin B2