STEREOCONTROLLED AND ENANTIOSELECTIVE SYNTHESIS OF THE BRANCHED 6-AMINO-4,6-DEOXYHEPTOPYRANURONIC ACID COMPONENT OF AMIPURIMYCIN

Authors
GARNER P YOO JU SARABU R KENNEDY VO YOUNGS WJ
Citation
P. Garner et al., STEREOCONTROLLED AND ENANTIOSELECTIVE SYNTHESIS OF THE BRANCHED 6-AMINO-4,6-DEOXYHEPTOPYRANURONIC ACID COMPONENT OF AMIPURIMYCIN, Tetrahedron, 54(32), 1998, pp. 9303-9316
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
32
Year of publication
1998
Pages
9303 - 9316
Database
ISI
SICI code
0040-4020(1998)54:32<9303:SAESOT>2.0.ZU;2-M
Abstract
A stereocontrolled and enantioselective synthesis of the branched 6-am ino-4,6-deoxyheptopyranuronic acid component of amipurimycin is report ed. Key stages in the synthesis include the stereodivergent assembly o f rile dihydropyrones 12 and 14 from serinal derivatives (S)-10 and (R )-10, elaboration of the tetrahydropyran ring to give 26 and 31, and f inally, introduction of the cis-2-aminocyclopentanecarboxylic acid moi ety to produce the diastereomeric peptides 28/29 and 32/33. (C) 1998 E lsevier Science Ltd. All rights reserved.