Abstract
A four-step synthesis of the Bristol-Myers' precursor, ethyl rel-(3 R, 4 R)-6,7-methylenedioxy-1-oxo-4-(3,4,5-trimethoxyphenyl)-1, 2,3,4-tetrahydronaphthalene-3-carboxylate, to (±)-podophyllotoxin is described in 40 % overall yield from ethyl 3,4,5-trimethoxycinnamate. Manganese(III) acetate mediated lactonization and Lewis acid induced heterocyclic rearrangement processes serve as the key steps in the synthesis of this intermediate.
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