The Intramolecular Carboxyarylation Approach to Podophyllotoxin

Aaron J. Reynolds,‡ Andrew J. Scott,† Craig I. Turner,† and Michael S. Sherburn*†
Research School of Chemistry, Australian National University, Canberra ACT 0200, Australia, and School of Chemistry, University of Sydney, Sydney NSW 2006, Australia
J. Am. Chem. Soc., 2003, 125 (40), pp 12108–12109
DOI: 10.1021/ja0376588
Publication Date (Web): September 13, 2003
Copyright © 2003 American Chemical Society
‡

 University of Sydney.

,
†

 Australian National University.

,
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, sherburn@rsc.anu.edu.au

Abstract

Abstract Image

Since 1960, only seven plant-derived anticancer drugs have received FDA approval for commercial production. Two are semisynthetic derivatives of podophyllotoxin. This paper describes concise, highly convergent, and conceptually novel approaches to (−)-podophyllotoxin and its enantiomer. These highly convergent syntheses feature a late-stage domino radical reaction to install the lactone ring and the pendant trimethoxyphenyl group.

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History

  • Published In Issue October 08, 2003
  • Received July 31, 2003

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