DIVERGENT ASYMMETRIC-SYNTHESIS OF ERYTHRO-3-AZIDO-1,2-EPOXIDES OR THREO-3-AZIDO-1,2-EPOXIDES FROM THE SAME 2,3-EPOXY-1-ALKANOL - A CONVENIENT SYNTHESIS OF STATINE AND ITS 3-EPIMER

Authors
BERTELLI L FIASCHI R NAPOLITANO E
Citation
L. Bertelli et al., DIVERGENT ASYMMETRIC-SYNTHESIS OF ERYTHRO-3-AZIDO-1,2-EPOXIDES OR THREO-3-AZIDO-1,2-EPOXIDES FROM THE SAME 2,3-EPOXY-1-ALKANOL - A CONVENIENT SYNTHESIS OF STATINE AND ITS 3-EPIMER, Gazzetta chimica italiana, 123(9), 1993, pp. 521-524
Citations number
12
Categorie Soggetti
Chemistry
Journal title
Gazzetta chimica italiana → ACNP
ISSN journal
00165603
Volume
123
Issue
9
Year of publication
1993
Pages
521 - 524
Database
ISI
SICI code
0016-5603(1993)123:9<521:DAOEOT>2.0.ZU;2-T
Abstract
A 2,3-epoxy-1-alkanol (obtained by Sharpless asymmetric epoxidation of the corresponding allylic alcohol), O-protected with a 2-methoxypropy l group, undergoes highly regioselective oxirane ring opening by attac k of azide ion at C-3 to afford a monoprotected azidodiol which can be elaborated to divergently give either threo-or erythro-3-azido- 1,2-e poxide. An application to the synthesis of the natural amino acid stat ine, 24, and of its 3-epimer, 26, is described.