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 inOrganic & biomolecular chemistry Vol. 5; no. 19; pp. 3201 - 3206
Main Authors Pullin, Robert D. C., Sellars, Jonathan D., Steel, Patrick G.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2007
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Podophyllotoxin - analogs & derivatives
Podophyllotoxin - chemical synthesis
Science & Technology
Silene - chemistry
Stereoisomerism
HOSOMI-SAKURAI REACTIONS
ROUTE
REAGENTS
PODOPHYLLOTOXIN
LIGNANS
ASYMMETRIC TOTAL-SYNTHESIS
NEOLIGNANS
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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
1477-0539
DOI:10.1039/b710370k