SYNTHESIS OF A NOVEL, CONFORMATIONALLY RESTRICTED ANALOG OF TRYPTOPHAN

被引：22

作者：

FRANCESCHETTI, L ^{[1
]}

GARZONABURBEH, A ^{[1
]}

MAHMOUD, MR ^{[1
]}

NATALINI, B ^{[1
]}

PELLICCIARI, R ^{[1
]}

机构：

[1] UNIV PERUGIA,IST CHIM FARMACEUT & TECN FARMACEUT,VIA LICEO 1,I-06123 PERUGIA,ITALY

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 19期

关键词：

CONFORMATIONALLY RESTRAINED TRYPTOPHAN ANALOG; DIAZOKETONE-BF3.ET2O CATALYZED INTRAMOLECULAR CYCLIZATION; CYCLOALK[B]INDOLONES;

D O I：

10.1016/S0040-4039(00)93413-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a new, conformationally restrained analog of tryptophan, 1,2,3,4-tetrahydro-2-amino-2-carboxy-cyclopent[b]indole (5) is described. The key step involves the BF3. Et2O catalyzed intramolecular cyclization of alpha-diazoketone 2b into the 1,2,3,4-tetrahydro-cyclopent[b]indol-2-one (3).

引用

页码：3185 / 3188

页数：4

共 15 条

[1] SYNTHESIS OF CYCLOPENT[B]INDOLONES [J].

BERGMAN, J ;

VENEMALM, L ;

GOGOLL, A .

TETRAHEDRON, 1990, 46 (17) :6067-6084

[2] A GENERAL ROUTE TO HYDANTOINS [J].

COKER, JN ;

MARTENS, TF ;

ROGERS, AO ;

ALLAN, GG ;

KOHLHASE, WL .

JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (09) :3201-&

[3] INTRAMOLECULAR CYCLIZATION OF ENAMINONES INVOLVING ARYLPALLADIUM COMPLEXES - SYNTHESIS OF CARBAZOLES [J].

IIDA, H ;

YUASA, Y ;

KIBAYASHI, C .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (15) :2938-2942

[4]

ISHIZUMI K, 1967, CHEM PHARM BULL, P863

[5]

JENNINGS KF, 1957, J CHEM SOC, P497

[6]

MAKI Y, 1973, CHEM PHARM BULL, V21, P2460

[7]

MANSKE RHF, 1931, CAN J RES, V4, P591

[8]

NAGASAKA T, 1977, CHEM PHARM BULL, P3023

[9] SELECTIVE OXIDATION OF SIDE-CHAIN AT C-3 OF INDOLES [J].

OIKAWA, Y ;

YONEMITSU, O .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (07) :1213-1216

[10]

PELLICCIARI R, 1990, EXCITATORY AMINO ACI, V6, P405

← 1 2 →