First enantioselective syntheses of (+)- and (-)-wilforonide by using chiral auxiliaries derived from the same chiral source.
[see structure]. The first enantioselective syntheses of both (+)-wilforonide (>98% ee) and (-)-wilforonide (>98% ee) have been accomplished by employing chiral auxiliaries derived from the same chiral source, (R)-pulegone. The bicyclic skeleton of wilforonide was constructed by using Mn(III)-based oxidative radical cyclization reactions of chiral beta-keto esters. The absolute configuration of natural wilforonide has been established to be (5aR,9aR).
Yang
D
D
Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong. yangdan@hku.hk
Xu
M
M
D002851:Chromatography, High Pressure Liquid; D006863:Hydrogen-Ion Concentration; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
D013729:Terpenes; C431468:wilforonide