A radical cyclisation approach to pyroglutamates

被引：46

作者：

Goodall, K ^{[1
]}

Parsons, AF ^{[1
]}

机构：

[1] UNIV YORK,DEPT CHEM,YORK YO1 5DD,N YORKSHIRE,ENGLAND

来源：

TETRAHEDRON | 1996年 / 52卷 / 19期

关键词：

D O I：

10.1016/0040-4020(96)00288-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of serine-derived N-(alpha-haloacetamido)dehydroalanine derivatives with tributyltin hydride in boiling benzene or toluene afforded pyroglutamates in 47-84% yield. The radical cyclisation reaction, which proceeded regioselectively in a disfavoured 5-endo-trig manner, was found to be most efficient when dichloro- and trichloroamides were employed as starting materials. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：6739 / 6758

页数：20

共 46 条

[1] 6-ENDO-TRIG RADICAL CYCLIZATIONS - SYNTHETIC APPROACHES TO THE A-B-RING OF (+/-)-FORSKOLIN
ANIES, C
BILLOT, L
LALLEMAND, JY
PANCRAZI, A
[J]. TETRAHEDRON LETTERS, 1995, 36 (40) : 7247 - 7250
[2] A NEW SYNTHETIC EQUIVALENT OF THE GLUTAMIC-ACID GAMMA-ANION AND ITS APPLICATION TO THE SYNTHESIS OF S-(+)-GAMMA-CARBOXYGLUTAMIC ACID
ATTWOOD, MR
CARR, MG
JORDAN, S
[J]. TETRAHEDRON LETTERS, 1990, 31 (02) : 283 - 284
[3] STEREOSPECIFIC SYNTHESIS OF (2S,4R)-[5,5,5-H-2(3)]-LEUCINE
AUGUST, RA
KHAN, JA
MOODY, CM
YOUNG, DW
[J]. TETRAHEDRON LETTERS, 1992, 33 (32) : 4617 - 4620
[4] BACHI MD, 1993, J ORG CHEM, V58, P5581
[5] (L)-PYROGLUTAMIC ACID AS A CHIRAL STARTING MATERIAL FOR ASYMMETRIC-SYNTHESIS
BALDWIN, JE
MOLONEY, MG
SHIM, SB
[J]. TETRAHEDRON LETTERS, 1991, 32 (10) : 1379 - 1380
[6] AMINO-ACID SYNTHESIS USING (L)-PYROGLUTAMIC ACID AS A CHIRAL STARTING MATERIAL
BALDWIN, JE
MIRANDA, T
MOLONEY, M
HOKELEK, T
[J]. TETRAHEDRON, 1989, 45 (23) : 7459 - 7468
[7] ENANTIOSELECTIVE KAINOID SYNTHESIS BY COBALT-MEDIATED CYCLIZATION OF AN AMINO-ACID DERIVATIVE
BALDWIN, JE
MOLONEY, MG
PARSONS, AF
[J]. TETRAHEDRON, 1990, 46 (20) : 7263 - 7282
[8] A NEW APPROACH TO KAINOIDS THROUGH TANDEM MICHAEL REACTION METHODOLOGY - APPLICATION TO THE ENANTIOSELECTIVE SYNTHESIS OF (+)-ALPHA-ALLOKAINIC AND (-)-ALPHA-ALLOKAINIC ACID AND TO THE FORMAL SYNTHESIS OF (-)-ALPHA-KAINIC ACID
BARCO, A
BENETTI, S
SPALLUTO, G
CASOLARI, A
POLLINI, GP
ZANIRATO, V
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) : 6279 - 6286
[9] SYNTHESIS OF NON-PROTEINOGENIC AMINO-ACIDS WITH 3 CHIRAL CENTERS
BOWLER, AN
DOYLE, PM
HITCHCOCK, PB
YOUNG, DW
[J]. TETRAHEDRON LETTERS, 1991, 32 (23) : 2679 - 2682
[10] CARDILLO B, 1994, HETEROCYCLES, V38, P2663

← 1 2 3 4 5 →