Asymmetric synthesis of the C(33)-C(37) fragment of amphotericin B

Citation
J. Tholander et Em. Carreira, Asymmetric synthesis of the C(33)-C(37) fragment of amphotericin B, HELV CHIM A, 84(3), 2001, pp. 613-622
Citations number
36
Categorie Soggetti
Chemistry & Analysis",Chemistry
Journal title
HELVETICA CHIMICA ACTA
ISSN journal
0018019X → ACNP
Volume
84
Issue
3
Year of publication
2001
Pages
613 - 622
Database
ISI
SICI code
0018-019X(2001)84:3<613:ASOTCF>2.0.ZU;2-2
Abstract
We have devised an expeditious. efficient, asymmetric synthesis of the C(33 )-C(37) fragment of amphotericin B that proceeds in 14 steps and 16% overal l yield from tiglic aldehyde ((E)-2-methylbut-2-enal) with complete stereoc ontrol. The route described herein relies on the application of recently de veloped methods in catalytic asymmetric synthesis for stereocontrol through enantio- and diastereoselective functionalization of a substituted sorbate derivative.