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.
Pullin
Robert D C
RD
Department of Chemistry, University of Durham, Science Laboratories, Durham, UK.
Sellars
Jonathan D
JD
Steel
Patrick G
PG
D011034:Podophyllotoxin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D029751:Silene / Q000737:chemistry*; D013237:Stereoisomerism
C415032:picropodophyllin; D011034:Podophyllotoxin