First enantioselective syntheses of (+)- and (-)-wilforonide by using chiral auxiliaries derived from the same chiral source

Authors
Citation
D. Yang et M. Xu, First enantioselective syntheses of (+)- and (-)-wilforonide by using chiral auxiliaries derived from the same chiral source, ORG LETT, 3(12), 2001, pp. 1785-1788
Citations number
31
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
1523-7060 → ACNP
Volume
3
Issue
12
Year of publication
2001
Pages
1785 - 1788
Database
ISI
SICI code
1523-7060(20010614)3:12<1785:FESO(A>2.0.ZU;2-2
Abstract
[GRAPHICS] The first enantioselective syntheses of both (+)-wilforonide (> 98% eel and (-)-wilforonide (>98% ee) have been accomplished by employing chiral auxil iaries derived from the same chiral source, (R)-pulegone. The bicyclic skel eton of wilforonide was constructed by using Mn(III) based oxidative radica l cyclization reactions of chiral beta -keto esters. The absolute configura tion of natural wilforonide has been established to be (5aR,9aR).