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

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

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.

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Bibliographic Details
Published in:Organic & biomolecular chemistry Vol. 5; no. 19; p. 3201
Main Authors: Pullin, Robert D C, Sellars, Jonathan D, Steel, Patrick G
Format: Journal Article
Language:English
Published: England 01-01-2007
Subjects:
Podophyllotoxin - analogs & derivatives
Podophyllotoxin - chemical synthesis
Silene - chemistry
Stereoisomerism
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Description
Summary: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.
ISSN:1477-0520
DOI:10.1039/b710370k