Download PDF
Synlett 2000; 2000(6): 0817-0819
DOI: 10.1055/s-2000-6694
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Stereoselective Synthesis of an Aminocyclopentitol Analog of α-l-Fucose via an Allylic Bromohydrin

Adrian Blaser* , Jean-Louis Reymond
  • *Department of Chemistry & Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland; Fax +41 31 631 80 57; E-mail: jean-louis.reymond@ioc.unibe.ch
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Selective opening of allylic epoxide 4 with lithium bromide in acetic acid provides an allylic bromohydrin (5). Chemo- and stereoselective hydrogenation of the corresponding benzyl carbamate 6 and intramolecular cyclization gives, after deprotection, (1R,2R,3R,4R,5R) 4-amino-5-methyl-cyclopentane-1,2,3-triol 3, an analog of α-l-fucose. This synthetic sequence provides one of the few stereoselective approaches to alpha-configurated aminocyclopentitols.

aminations - amino alcohols - carbohydrates - glycosidases - stereoselective synthesis