A New Synthesis of Aflatoxin M1

Article abstract of DOI:10.1021/ja00402a039

Starting with the known and readily available phloroglucinol monobenzenesulfonate (4) and 1,4-anhydroerythritol (7), we prepared aflatoxin M₁ (1) in 13 steps with an overall yield of 5percent.The critical features of this second synthesis of aflatoxin M₁ (1) include a novel approach to the tricyclic phenol 21 containing the ABC ring system, a regioselective hydrogenolysis of the benzyl protecting group at C₆ in 16, and removal of the second benzyl group in 20 by Birch reduction.Neither the 1,3,5-trialkoxy-substituted benzene ring nor the vinyl ether function present in 20 were affected in the latter operation.