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

Robert D C Pullin; Jonathan D Sellars; Patrick G Steel

doi:10.1039/b710370k

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

Org Biomol Chem. 2007 Oct 7;5(19):3201-6. doi: 10.1039/b710370k. Epub 2007 Aug 31.

Authors

Robert D C Pullin¹, Jonathan D Sellars, Patrick G Steel

Affiliation

¹ Department of Chemistry, University of Durham, Science Laboratories, Durham, UK.

PMID: 17878979
DOI: 10.1039/b710370k

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Podophyllotoxin / analogs & derivatives*
Podophyllotoxin / chemical synthesis
Silene / chemistry*
Stereoisomerism

Substances

picropodophyllin
Podophyllotoxin