Iodine-catalyzed chemoselective dehydrogenation and aromatization of tetrahydro-β-carbolines: A short synthesis of Kumujian-C, Eudistomin-U, Norharmane, Harmane Harmalan and Isoeudistomine-M

被引：26

作者：

Gaikwad, Sunil ^{[1
]}

Kamble, Dayanand ^{[1
]}

Lokhande, Pradeep ^{[1
]}

机构：

[1] Savitribai Phule Pune Univ, Ctr Adv Studies, Dept Chem, Pune 411007, Maharashtra, India

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 25期

关键词：

Dehydrogenation; Aromatization; Iodine; Carbolines; Kumujian-C; Eudistomin-U; BIOLOGICAL EVALUATION; CARBAZOLE ALKALOIDS; EFFICIENT SYNTHESIS; ROOM-TEMPERATURE; FORMAL SYNTHESIS; DERIVATIVES; UTILITY; DESIGN; HETEROCYCLES; CYCLIZATION;

D O I：

10.1016/j.tetlet.2018.04.043

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Temperature controlled chemoselective dehydrogenation and aromatization of tetrahydro-beta-carbolines, using molecular I-2 and H2O2, in DMSO solvent affords a practical access to a series of corresponding 3,4-dihydro-beta-carbolines and beta-carbolines respectively. This method has been successfully employed in the short synthesis of Kumujian-C, Eudistomin-U, Norharmane Harmane Harmalan and Isoeudistomin-M. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：2387 / 2392

页数：6

共 65 条

[1]

[Anonymous], 2002, ANGEW CHEM

[2] Synthesis and anti-leishmanial evaluation of 1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline derivatives against Leishmania infantum [J].

Ashok, Penta ;

Chander, Subhash ;

Tejeria, Ana ;

Garcia-Calvo, Laura ;

Balana-Fouce, Rafael ;

Murugesan, Sankaranarayanan .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 123 :814-821

[3] EUDISTOMIN-U AND ISOEUDISTOMIN U, NEW ALKALOIDS FROM THE CARIBBEAN ASCIDIAN LISSOCLINUM-FRAGILE [J].

BADRE, A ;

BOULANGER, A ;

ABOUMANSOUR, E ;

BANAIGS, B ;

COMBAUT, G ;

FRANCISCO, C .

JOURNAL OF NATURAL PRODUCTS, 1994, 57 (04) :528-533

[4] Toxicological profile and acetylcholinesterase inhibitory potential of Palicourea deflexa, a source of β-carboline alkaloids [J].

Bertelli, Pablo Ricardo ;

Biegelrneyer, Renata ;

Rico, Eduardo Pacheco ;

Klein-Junior, Luiz Carlos ;

Toson, Natally S. B. ;

Minetto, Luciane ;

Bordignon, Sergio A. L. ;

Gasper, Andre L. ;

Moura, Sidnei ;

de Oliveira, Diogo L. ;

Henriques, Amelia T. .

COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY C-TOXICOLOGY & PHARMACOLOGY, 2017, 201 :44-50

[5] BETA-CARBOLINES - SYNTHESIS AND NEUROCHEMICAL AND PHARMACOLOGICAL ACTIONS ON BRAIN BENZODIAZEPINE RECEPTORS [J].

CAIN, M ;

WEBER, RW ;

GUZMAN, F ;

COOK, JM ;

BARKER, SA ;

RICE, KC ;

CRAWLEY, JN ;

PAUL, SM ;

SKOLNICK, P .

JOURNAL OF MEDICINAL CHEMISTRY, 1982, 25 (09) :1081-1091

[6] β-Carboline alkaloids:: Biochemical and pharmacological functions [J].

Cao, Rihui ;

Peng, Wenlie ;

Wang, Zihou ;

Xu, Anlong .

CURRENT MEDICINAL CHEMISTRY, 2007, 14 (04) :479-500

[7] Discovery of McbB, an Enzyme Catalyzing the β-Carboline Skeleton Construction in the Marinacarboline Biosynthetic Pathway [J].

Chen, Qi ;

Ji, Changtao ;

Song, Yongxiang ;

Huang, Hongbo ;

Ma, Junying ;

Tian, Xinpeng ;

Ju, Jianhua .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (38) :9980-9984

[8] On the mechanisms of oxidation of organic sulfides by H2O2 in aqueous solutions [J].

Chu, JW ;

Trout, BL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (03) :900-908

[9]

COUTTS RT, 1984, HETEROCYCLES, V22, P131

[10] A novel palladium-catalyzed synthesis of β-carbolines:: application in total synthesis of naturally occurring alkaloids [J].

Dantale, SW ;

Söderberg, BCG .

TETRAHEDRON, 2003, 59 (29) :5507-5514

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