Stereoselective synthesis of (3S,4R)-3,4-dimethyl-(S)-glutamine and the absolute stereochemistry of the natural product from papuamides and callipeltin

Authors
Okamoto, N Hara, O Makino, K Hamada, Y
Citation
N. Okamoto et al., Stereoselective synthesis of (3S,4R)-3,4-dimethyl-(S)-glutamine and the absolute stereochemistry of the natural product from papuamides and callipeltin, TETRAHEDR-A, 12(9), 2001, pp. 1353-1358
Citations number
17
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
12
Issue
9
Year of publication
2001
Pages
1353 - 1358
Database
ISI
SICI code
0957-4166(20010611)12:9<1353:SSO(AT>2.0.ZU;2-T
Abstract
(3S,4R)-3,4-Dimethyl-(S)-glutamine, a common component of cyclodepsipeptide s, papuamide A and callipeltin A, was stereoselectively prepared from (S)-p yroglutamic acid. The stereostructure of natural dimethylglutamine was unam biguously confirmed to be (2S,3S,4R) by comparison of the CD and NMR spectr a of the synthetic 3,4-dimethylpyroglutamic acid with the hydrolysate of ca llipeltin A. (C) 2001 Elsevier Science Ltd. All rights reserved.