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Issue 11, 1993
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A practical synthesis of the anti-tumour agent 2-methyl-4-deoxyisopicropodophyllotoxin and related podophyllin analogues

Abstract

We describe an efficient, six-stage synthesis of 2-methyl-4-deoxyisopicropodophyllotoxin, which proceeds via a Diels–Alder cycloaddition between 2-methylmaleic anhydride and the orthoquinodimethane generated by treatment of 5-[1-acetoxy-1-(3′,4′,5′-trimethoxyphenyl)methyl]-6-trimethylsilylmethyl-1,3-benzodioxole with silica gel at 60 °C. The podophyllin was converted into a number of 4′-ester derivatives. This procedure was also used to prepare a diazapodophyllin via the use of 4-phenyl-1,2,4-triazoline-3,5-dione as dienophile.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1993, 1235-1238
Article type
Paper

A practical synthesis of the anti-tumour agent 2-methyl-4-deoxyisopicropodophyllotoxin and related podophyllin analogues

A. R. Beard, S. J. Hazell, J. Mann and C. Palmer, J. Chem. Soc., Perkin Trans. 1, 1993, 1235
DOI: 10.1039/P19930001235

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