The chemistry of indoles part 91 -: Preparations of melatonin and 1-hydroxymelatonin, and its novel nucleophilic dimerization to (±)-3a,3a′-bispyrrolo[2,3-b]indoles

被引：38

作者：

Somei, M ^{[1
]}

Oshikiri, N ^{[1
]}

Hasegawa, M ^{[1
]}

Yamada, F ^{[1
]}

机构：

[1] Kanazawa Univ, Fac Pharmaceut Sci, Kanazawa, Ishikawa 9200934, Japan

来源：

HETEROCYCLES | 1999年 / 51卷 / 06期

关键词：

D O I：

10.3987/COM-99-8542

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A unique synthetic method for melatonin was established through biologically promising synthetic intermediates, 1-Hydroxymelatonin was prepared as crystals for the first time. It reacted with 85% formic acid to give (+/-)-3a,3a'-bispyrrolo[2,3-b]indole compound, whose structure was unequivocally determined by X-Ray crystallographic analysis.

引用

页码：1237 / +

页数：7

共 28 条

[1] BIOGENETIC-TYPE SYNTHESIS OF CALYCANTHACEOUS ALKALOIDS [J].

HALL, ES ;

MCCAPRA, F ;

SCOTT, AI .

TETRAHEDRON, 1967, 23 (10) :4131-&

[2]

Hasegawa M, 1996, HETEROCYCLES, V43, P2333

[3]

HAYASHI H, IN PRESS HETEROCYCLE

[4] TOTAL SYNTHESIS OF CALYCANTHACEOUS ALKALOIDS [J].

HENDRICKSON, JB ;

GOSCHKE, R ;

REES, R .

TETRAHEDRON, 1964, 20 (03) :565-&

[5]

HINO T, 1963, TETRAHEDRON LETT, P1757

[6]

HODSON HF, 1961, P CHEM SOC LONDON, P465

[7] Stereocontrolled total syntheses of meso-chimonanthine and meso-calycanthine via a novel samarium mediated reductive dialkylation [J].

Link, JT ;

Overman, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (34) :8166-8167

[8] OXIDATIVE DIMERIZATION OF NB-ACYLTRYPTOPHANS TOTAL SYNTHESIS AND ABSOLUTE-CONFIGURATION OF DITRYPTOPHENALINE [J].

NAKAGAWA, M ;

SUGUMI, H ;

KODATO, S ;

HINO, T .

TETRAHEDRON LETTERS, 1981, 22 (52) :5323-5326

[9]

Pierpaoli W, 1991, Aging (Milano), V3, P99

[10]

SCHMID HA, 1993, GERONTOLOGY, V39, P189

← 1 2 3 →