Synthesis of the proposed structure and revision of stereochemistry of kaitocephalin

被引：35

作者：

Okue, M

Kobayashi, H

Shin-ya, K

Furihata, K

Hayakawa, Y

Seto, H

Watanabe, H ^{[1
]}

Kitahara, T

机构：

[1] Univ Tokyo, Grad Sch Agr & Life Sci, Dept Appl Biol Chem, Bunkyo Ku, Tokyo 1138657, Japan

[2] Univ Tokyo, Inst Mol & Cellular Biosci, Bunkyo Ku, Tokyo 1130032, Japan

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 05期

关键词：

kaitocephalin; total synthesis; NMDA antagonist; AMPA KA antagonist;

D O I：

10.1016/S0040-4039(01)02254-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective total synthesis of the proposed structure of kaitocephalin (1) was accomplished starting from L-proline and D- and L-serines. How ever, its H-1 NMR spectral data and retention time oil HPLC were not identical with those of authentic natural kaitocephalin. The revised stereochemistry of natural kaitocephalin. (2R)-isomer (16), was inferred from further experiments employing diastereomers and model compounds. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：857 / 860

页数：4

共 16 条

[1]

ANELLI PL, 1987, J ORG CHEM, V52, P2559

[2]

BECK AK, 1993, ORG SYNTH, V72, P62

[3] ULTRASOUND IN ORGANIC SYNTHESES .19. FURTHER-STUDIES ON THE CONJUGATE ADDITIONS TO ELECTRON DEFICIENT OLEFINS IN AQUEOUS-MEDIA [J].