Short synthesis of (3S,6S,9S)-2-oxo-3-(N-Boc-amino)-1-azabicyclo[4.3.0]nonane-9-carboxylic acid methyl ester: Tandem cyclization protocol

被引：24

作者：

Kim, HO ^{[1
]}

Kahn, M ^{[1
]}

机构：

[1] UNIV WASHINGTON,DEPT PATHOBIOL,SEATTLE,WA 98195

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 37期

关键词：

D O I：

10.1016/S0040-4039(97)01492-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise enantioselective synthesis of (3S,6S,9S)-2-oxo-3-(N-Boc-amino)-1-azabicyclo[4.3.0]nonane-9-carboxylic acid methyl ester from N-protected glutamic acid is described. (C) 1997 Elsevier Science Ltd.

引用

页码：6483 / 6484

页数：2

共 8 条

[1]

HARRIS BD, 1987, TETRAHEDRON LETT, V25, P2837

[2]

KAHN M, 1993, SYNLETT, P821

[3]

KAHN M, 1993, TETRAHEDRON, V49, P3444

[4] COPPER (I)-PROMOTED CONDENSATION OF ALPHA-AMINO-ACIDS WITH BETA-KETO THIO ESTERS - SYNTHESIS OF N-ACYLATED L-LEUCINE DERIVATIVES CONTAINING (S)-4-HYDROXY-5-METHYL-3-OXOHEXANOIC AND (S)-4-HYDROXY-2,5-DIMETHYL-3-OXOHEXANOIC ACID [J].

KIM, HO ;

OLSEN, RK ;

CHOI, OS .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (20) :4531-4536

[5]

KIM HO, IN PRESS TETRAHEDRON

[6] Conformationally restricted peptide mimetics: The incorporation of 6,5-bicyclic lactam ring skeletons into peptides [J].

Li, WH ;

Hanau, CE ;

dAvignon, A ;

Moeller, KD .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (25) :8155-8170

[7] SYNTHESIS OF ENANTIOPURE ALPHA,OMEGA-DIAMINO DICARBOXYLATES AND AZABICYCLOALKANE AMINO-ACIDS BY CLAISEN CONDENSATION OF ALPHA-[N-(PHENYLFLUORENYL)AMINO] DICARBOXYLATES [J].

LOMBART, HG ;

LUBELL, WD .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6147-6149

[8] SYNTHESIS OF RETROHYDROXAMATE ANALOGS OF THE MICROBIAL IRON-TRANSPORT AGENT FERRICHROME [J].

OLSEN, RK ;

RAMASAMY, K .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (13) :2264-2271

← 1 →