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Synthesis 1991; 1991(4): 275-277
DOI: 10.1055/s-1991-26444
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Anticancer Agent Development; 6.1 Application of the Heterocycle Annulation-Rearrangement Strategy in the Synthesis of a Podophyllotoxin Precursor

John R. Peterson* , Hoang D. Do, Robin D. Rogers
  • *Department of Pharmacognosy and the Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, MS 38677, USA
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Publication Date:
29 April 2002 (online)

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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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