Synthesis of the 3a-(3-indolyl)-1,2,3,3a,8,8a-hexa-hydropyrrolo[2,3-b] indole core of leptosins D-F

被引：12

作者：

Crich, D ^{[1
]}

Fredette, E ^{[1
]}

Flosi, WJ ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

HETEROCYCLES | 1998年 / 48卷 / 03期

关键词：

D O I：

10.3987/COM-97-8063

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Fischer indole reaction of aldehyde and phenyl hydrazine in the presence of zinc chloride smoothly provides the core structure of the leptosins D-F in good to excellent yield.

引用

页码：545 / 547

页数：3

共 14 条

[1] ENANTIOSPECIFIC SYNTHESIS WITH AMINO-ACIDS .1. TRYPTOPHAN AS A CHIRON FOR THE SYNTHESIS OF ALPHA-SUBSTITUTED TRYPTOPHAN DERIVATIVES [J].

BOURNE, GT ;

CRICH, D ;

DAVIES, JW ;

HORWELL, DC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (07) :1693-1699

[2] CYCLIC TAUTOMERS OF TRYPTOPHAN - ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESIS OF BETA-SUBSTITUTED AND ALPHA-BETA-DISUBSTITUTED DERIVATIVES OF TRYPTOPHAN [J].

BRUNCKO, M ;

CRICH, D .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15) :4239-4249

[3] CHEMISTRY OF CYCLIC TAUTOMERS OF TRYPTOPHAN - FORMATION OF A QUATERNARY CENTER AT C3A AND TOTAL SYNTHESIS OF THE MARINE ALKALOID (+)-ENT-DEBROMOFLUSTRAMINE-B [J].

BRUNCKO, M ;

CRICH, D ;

SAMY, R .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) :5543-5549

[4] THE CHEMISTRY OF CYCLIC TAUTOMERS OF TRYPTOPHAN - TOTAL SYNTHESIS OF (+)-(ENT)-PSEUDOPHRYNAMINOL [J].

CRICH, D ;

PAVLOVIC, AB ;

SAMY, R .

TETRAHEDRON, 1995, 51 (23) :6379-6384

[5] CONFORMATIONAL-ANALYSIS OF SUBSTITUTED HEXAHYDROPYRROLO[2,3-B]INDOLES AND RELATED SYSTEMS - AN UNUSUAL EXAMPLE OF HINDERED ROTATION ABOUT SULFONAMIDE S-N BONDS - AN X-RAY CRYSTALLOGRAPHIC AND NMR-STUDY [J].

CRICH, D ;

BRUNCKO, M ;

NATARAJAN, S ;

TEO, BK ;

TOCHER, DA .

TETRAHEDRON, 1995, 51 (08) :2215-2228

[6] TOTAL SYNTHESIS OF SPORIDESMIN-A [J].

KISHI, Y ;

NAKATSUKA, S ;

FUKUYAMA, T ;

HAVEL, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (19) :6493-6495

[7] NEW METHOD FOR SYNTHESIS OF EPIDITHIODIKETOPIPERAZINES [J].

KISHI, Y ;

FUKUYAMA, T ;

NAKATSUKA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (19) :6490-6492

[8] STUDIES ON METABOLITES OF VERTICILLIUM-SP STRUCTURES OF VERTICILLINS A,B AND C 1ALPHA [J].

MINATO, H ;

MATSUMOTO, M ;

KATAYAMA, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (17) :1819-1825

[9]

NAKATSUKA S, 1974, TETRAHEDRON LETT, P1549, DOI 10.1016/S0040-4039(01)93133-8

[10]

Robinson B., 1982, The Fischer Indole Synthesis

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