A SUCCESSFUL ACID-PROMOTED ASYMMETRIC PICTET-SPENGLER REACTION OF N-A-BOC PROTECTED TRYPTOPHANS - EFFECT OF THE BOC GROUP ON REACTIVITY AND STEREOSELECTIVITY

被引：10

作者：

ZHANG, PW ^{[1
]}

COOK, JM ^{[1
]}

机构：

[1] UNIV WISCONSIN,DEPT CHEM,MILWAUKEE,WI 53201

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 39期

关键词：

D O I：

10.1016/0040-4039(95)01448-Q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-a-BOC protected tryptophans 1 and 2 successfully undergo the Pictet-Spengler cyclization with a series of aldehydes in the presence of an acid catalyst (p-TSA) to furnish a mixture of trans and cis 1,2,3,4-tetrahydro-beta-carbolines (3 and 4). During removal of the BOC function with TFA, the mixture of trans (3) and cis (4) isomers was enantiospecifically converted into the trans N-a-H 1,2,3,4-tetrahydro-beta-carboline 5, a key intermediate for the construction of N-a-H substituted sarpagine alkaloids.

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页码：6999 / 7002

页数：4

相关论文

共 22 条

[11] INTRAMOLECULAR PICTET-SPENGLER REACTION OF N-ALKOXYTRYPTAMINES .3. STEREOSELECTIVE SYNTHESIS OF (-)-DEBROMOEUDISTOMIN-L AND (-)-O-METHYLDEBROMOEUDISTOMIN-E AND THEIR STEREOISOMERS [J].

HERMKENS, PHH ;

VONMAARSEVEEN, JH ;

OTTENHEIJM, HCJ ;

KRUSE, CG ;

SCHEEREN, HW .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (13) :3998-4006

[12] TOTAL SYNTHESIS OF (+)-FUMITREMORGIN-B, ITS EPIMERIC ISOMERS, AND DEMETHOXY DERIVATIVES [J].

KODATO, S ;

NAKAGAWA, M ;

HONGU, M ;

KAWATE, T ;

HINO, T .

TETRAHEDRON, 1988, 44 (02) :359-377

[13] SYNTHETIC APPROACH TO THE TOTAL SYNTHESIS OF FUMITREMORGINS-II SYNTHESIS OF OPTICALLY-ACTIVE PENTACYCLIC INTERMEDIATES AND THEIR DEHYDROGENATION [J].

NAKAGAWA, M ;

FUKUSHIMA, H ;

KAWATE, T ;

HONGU, M ;

KODATO, S ;

UNE, T ;

TANIGUCHI, M ;

HINO, T .

TETRAHEDRON LETTERS, 1986, 27 (28) :3235-3238

[14]

REDDY MS, 1994, TETRAHEDRON LETT, P5413

[15]

SHIMIZU M, 1984, CHEM PHARM BULL, V32, P1313

[16] APPROACHES TO THE TETRACYCLIC EUDISTOMINS - THE SYNTHESIS OF N(10)-ACETYLEUDISTOMIN-L [J].

STILL, IWJ ;

STRAUTMANIS, JR .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1990, 68 (08) :1408-1419

[17] GENERAL-METHOD FOR THE ASSIGNMENT OF STEREOCHEMISTRY OF 1,3-DISUBSTITUTED 1,2,3,4-TETRAHYDRO-BETA-CARBOLINES BY C-13 SPECTROSCOPY [J].

UNGEMACH, F ;

SOERENS, D ;

WEBER, R ;

DIPIERRO, M ;

CAMPOS, O ;

MOKRY, P ;

COOK, JM ;

SILVERTON, JV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (23) :6976-6984

[18] STEREOSPECIFIC SYNTHESIS OF TRANS-1,3-DISUBSTITUTED-1,2,3,4-TETRAHYDRO-BETA-CARBOLINES [J].

UNGEMACH, F ;

DIPIERRO, M ;

WEBER, R ;

COOK, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (01) :164-168

[19]

WHALEY WM, 1951, ORG REACTIONS, V6, P151

[20] GENERAL-APPROACH TO THE SYNTHESIS OF MACROLINE-RELATED ALKALOIDS - STEREOSPECIFIC TOTAL SYNTHESIS OF (-)-ALSTONERINE [J].

ZHANG, LH ;

COOK, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :4088-4090