Quinone approaches toward the synthesis of aflatoxin B(2).
[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.
Noland
W E
WE
Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
Kedrowski
B L
BL
D000348:Aflatoxins / Q000138:chemical synthesis*; D001230:Aspergillus / Q000737:chemistry; D002614:Chelating Agents; D009183:Mycotoxins / Q000138:chemical synthesis*; D016877:Oxidants; D011809:Quinones / Q000737:chemistry*; D013237:Stereoisomerism
D000348:Aflatoxins; D002614:Chelating Agents; D009183:Mycotoxins; D016877:Oxidants; D011809:Quinones; C029753:aflatoxin B2