Highly enantioselective synthesis of S-(+)-calycotomine from L-ascorbic acid and absolute assignment of its enantiomeric excess

Authors
Czarnocki, Z Ziolkowski, M Leniewski, A Maurin, JK
Citation
Z. Czarnocki et al., Highly enantioselective synthesis of S-(+)-calycotomine from L-ascorbic acid and absolute assignment of its enantiomeric excess, ENANTIOMER, 4(2), 1999, pp. 71-77
Citations number
17
Categorie Soggetti
Chemistry
Journal title
ENANTIOMER
ISSN journal
10242430 → ACNP
Volume
4
Issue
2
Year of publication
1999
Pages
71 - 77
Database
ISI
SICI code
1024-2430(1999)4:2<71:HESOSF>2.0.ZU;2-O
Abstract
S-(+)-Calycotomine 1 was obtained in good chemical yield and of high optica l purity in a multi-step reaction sequence starting from L-ascorbic acid (v itamin C). Enantiomeric integrity of (S)-(-)-N-acetylcalycotomine 17 and S- (+)-calycotomine 1 was established by an absolute method, using F-19 NMR of their Mosher's acid derivatives.