Journal of the American Chemical Society p. 3497 - 3501 (1981)
Update date:2022-07-29
Topics:
Buechi, George
Francisco, Manuel A.
Liesch, Jerrold M.
Schuda, Paul F.
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.
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