SYNTHESIS OF (2S,3R)-3-AMINO-2-HYDROXYDECANOIC ACID AND (3R,4R)-3-AMINO-4-HYDROXYAZEPANE FROM D-ISOASCORBIC ACID

Authors
TUCH A SANIERE M LEMERRER Y DEPEZAY JC
Citation
A. Tuch et al., SYNTHESIS OF (2S,3R)-3-AMINO-2-HYDROXYDECANOIC ACID AND (3R,4R)-3-AMINO-4-HYDROXYAZEPANE FROM D-ISOASCORBIC ACID, Tetrahedron : asymmetry, 7(10), 1996, pp. 2901-2909
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
10
Year of publication
1996
Pages
2901 - 2909
Database
ISI
SICI code
0957-4166(1996)7:10<2901:SO(AA(>2.0.ZU;2-K
Abstract
Taking advantage of the high functionality of an enantiopure protected syn-2R-amino-1,3,4-triol derivative, easily available on a multigram scale from D-isoascorbic acid, several biologically active compounds h ave been synthesized such as the (2S,3R)-3-amino-2-hydroxydecanoic aci d (AHDA), the N-terminal moiety of microginin, and the (3R,4R)-3-amino -4-hydroxyazepane, the ophiocordin and balanol core structure. Copyrig ht (C) 1996 Elsevier Science Ltd