MODEL STUDIES RELATED TO THE TOTAL SYNTHESIS OF THE FUMITREMORGINS - THE PICTET-SPENGLER CYCLIZATION AND THE FORMATION AND INTRAMOLECULAR ACYLATION OF A 1,2-DIHYDRO-BETA-CARBOLINE DERIVATIVE

被引：15

作者：

HARRISON, DM ^{[1
]}

SHARMA, RB ^{[1
]}

机构：

[1] UNIV ULSTER,DEPT CHEM,COLERAINE BT52 1SA,NORTH IRELAND

来源：

TETRAHEDRON | 1993年 / 49卷 / 15期

关键词：

D O I：

10.1016/S0040-4020(01)89899-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparations of the tetrahydro-beta-carbolines 8, 9b, and 9d are described. The Pictet-Spengler reaction of L-tryptophyl-L-proline methyl ester with 3-methylbutanal gave the tetrahydro-beta-carbolines 20 and 21; subsequent acid-catalysed cyclisation afforded the fumitremorgin analogues 22 and 23. The 2-(p-toluenesulphonyl)tetrahydro-beta-carboline 27a furnished the unsaturated pentacycle 28a upon treatment with alkali.

引用

页码：3165 / 3184

页数：20

共 40 条

[1] ON THE ASSIGNMENT OF STEREOCHEMISTRY OF 1,3-DISUBSTITUTED TETRAHYDRO-BETA-CARBOLINES USING C-13 NMR-SPECTROSCOPY [J].

BAILEY, PD ;

HOLLINSHEAD, SP .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (22) :1575-1576

[2] EXCEPTIONAL STEREOCHEMICAL CONTROL IN THE PICTET-SPENGLER REACTION [J].

BAILEY, PD ;

HOLLINSHEAD, SP ;

MCLAY, NR .

TETRAHEDRON LETTERS, 1987, 28 (43) :5177-5180

[3] A STEREOSELECTIVE ENTRY TO THE FUMITREMORGINS [J].

BAILEY, PD ;

HOLLINSHEAD, SP ;

MCLAY, NR .

TETRAHEDRON LETTERS, 1989, 30 (46) :6421-6422

[4] STEREOSELECTIVE SYNTHESIS OF DESMETHOXY-(+)-VERRUCULOGEN TR-2 [J].

BOYD, SA ;

THOMPSON, WJ .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (09) :1790-1794

[5]

DAVIES JS, 1977, TETRAHEDRON LETT, P1453

[6]

GAJEWSKI JJ, 1990, ADV MOL MODELLING, V2, P65

[7] OBSERVATIONS ON THE PICTET-SPENGLER SYNTHESIS OF 1,2,3,4-TETRAHYDRO-BETA-CARBOLINES [J].

GRIGG, R ;

GUNARATNE, HQN ;

MCNAGHTEN, E .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (01) :185-187

[8] THE FORMATION AND INTRAMOLECULAR ACYLATION OF A 1,2-DIHYDRO-BETA-CARBOLINE DERIVATIVE - A MODEL SEQUENCE FOR THE TOTAL SYNTHESIS OF FUMITREMORGINS [J].

HARRISON, DM ;

SHARMA, RB .

TETRAHEDRON LETTERS, 1986, 27 (04) :521-524

[9] THE REACTION OF 3-METHYLBUT-2-ENAL WITH TRYPTAMINE AND ITS DERIVATIVES - A SUGGESTION FOR THE BIOSYNTHESIS OF AUSTAMIDE [J].

HARRISON, DM .

TETRAHEDRON LETTERS, 1981, 22 (26) :2501-2504

[10] NEW SYNTHESES OF RACEMIC TRYPTOPHANS [J].

HENGARTNER, U ;

BATCHO, AD ;

BLOUNT, JF ;

LEIMGRUBER, W ;

LARSCHEID, ME ;

SCOTT, JW .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (22) :3748-3752

← 1 2 3 4 →