DE-NOVO ASYMMETRIC-SYNTHESIS OF 2 5-AMINO-5,6-DIDEOXY-D-ALLOSE DERIVATIVES

Authors
DEFOIN A SARAZIN H STREHLER C STREITH J
Citation
A. Defoin et al., DE-NOVO ASYMMETRIC-SYNTHESIS OF 2 5-AMINO-5,6-DIDEOXY-D-ALLOSE DERIVATIVES, Tetrahedron letters, 35(31), 1994, pp. 5653-5656
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
31
Year of publication
1994
Pages
5653 - 5656
Database
ISI
SICI code
0040-4039(1994)35:31<5653:DAO25D>2.0.ZU;2-Q
Abstract
Diels-Alder cycloaddition of sorbic aldehyde derivative 9 and of sorbi c acid 10 with the chiral chloro-nitroso dienophile 7 led with excelle nt regio- and diastereoselectivity to the chiral cycloadducts 11a and 12, respectively. Catalytic osmylation of their Bzl-derivatives 11b an d 13b, followed by reductive cleavage of the N-O bonds, gave ultimatel y the chiral aminoallose derivatives D-5 and D-6 which are potential g lycosidase inhibitors.