Issue 19, 2007
From the journal:

Organic & Biomolecular Chemistry

Silenes in organic synthesis: a concise synthesis of (±)-epi-picropodophyllin†

Robert D. C. Pullin,a   Jonathan D. Sellarsa  and  Patrick G. Steel*a  

* Corresponding authors

a Department of Chemistry, University of Durham, Science Laboratories, South Road, Durham, UK
E-mail: p.g.steel@durham.ac.uk

Abstract

A concise, seven step synthesis of the aryl tetralin lignan lactone epi-picropodophyllin from piperonal is described. The key steps are a silene diene Diels–Alder reaction and the Hosomi–Sakurai reaction of the resultant silacyclohexene.

Graphical abstract: Silenes in organic synthesis: a concise synthesis of (±)-epi-picropodophyllin

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Article information

DOI
https://doi.org/10.1039/B710370K
Article type
Paper
Submitted
09 Jul 2007
Accepted
13 Aug 2007
First published
31 Aug 2007

Org. Biomol. Chem., 2007,5, 3201-3206

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Silenes in organic synthesis: a concise synthesis of (±)-epi-picropodophyllin

R. D. C. Pullin, J. D. Sellars and P. G. Steel, Org. Biomol. Chem., 2007, 5, 3201 DOI: 10.1039/B710370K

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