A NEW AND HIGHLY STEREOSELECTIVE SYNTHESIS OF POLYHYDROXYINDOLIZIDINES FROM 4-OCTULOSE DERIVATIVES

Authors
IZQUIERDO I PLAZA MT ROBLES R MOTA AJ
Citation
I. Izquierdo et al., A NEW AND HIGHLY STEREOSELECTIVE SYNTHESIS OF POLYHYDROXYINDOLIZIDINES FROM 4-OCTULOSE DERIVATIVES, Tetrahedron : asymmetry, 9(6), 1998, pp. 1015-1027
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
6
Year of publication
1998
Pages
1015 - 1027
Database
ISI
SICI code
0957-4166(1998)9:6<1015:ANAHSS>2.0.ZU;2-9
Abstract
S,6R,7R,8R,8aR)-1,2,6,7,8-Pentahydroxyindolizidine 12 and (1R,6R,7R,8R ,8aR)-1,6,7,8-tetrahydroxyindolizidine (1,6-diepicastanospermine, 24) have been stereoselectively synthesized from the important key interme diates 1,4-dideoxy-1,4-imino-D-erythro-L-altro-octitol 7 and 1,2,4-tri deoxy-1,4-imino-D-glycero-D-talo-octitol 20 in three steps. Compounds 7 and 20 were readily obtained from ne-beta-D-glycero-D-galacto-oct-4- ulo-4,8-pyranose 1 and isopropylidene-beta-D-manno-oct-4-ulo-4,8-pyran ose 13 in four steps, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.