Scalable Total Syntheses of N-Linked Tryptamine Dimers by Direct Indole-Aniline Coupling: Psychotrimine and Kapakahines B and F

被引：159

作者：

Newhouse, Timothy ^{[1
]}

Lewis, Chad A. ^{[1
]}

Eastman, Kyle J. ^{[1
]}

Baran, Phil S. ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 20期

基金：

加拿大健康研究院;

关键词：

ENANTIOSPECIFIC TOTAL-SYNTHESIS; LASER FLASH-PHOTOLYSIS; PALLADIUM-CATALYZED HETEROANNULATION; NUCLEOPHILIC AROMATIC-SUBSTITUTION; STEREOCONTROLLED TOTAL-SYNTHESIS; CONCISE TOTAL-SYNTHESIS; NATURAL-PRODUCTS; NITRENIUM IONS; OXIDATIVE POLYMERIZATION; CELOGENTIN-C;

D O I：

10.1021/ja1009458

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This report details the invention of a method to enable syntheses of psychotrimine (1) and the kapakahines F and B (2, 3) on a gram scale and in a minimum number of steps. Mechanistic inquiries are presented for the key enabling quaternization of indole at the C3 position by electrophilic attack of an activated aniline species. Excellent chemo-, regio-, and diastereoselectivities are observed for reactions with o-iodoaniline, an indole cation equivalent. Additionally, the scope of this reaction is broad with respect to the tryptamine and aniline components. The anti-cancer profiles of 1-3 have also been evaluated.

引用

页码：7119 / 7137

页数：19

共 155 条

[1]

Adam W., 2000, PEROXIDE CHEM, P542

[2] Pyrrole-2-carboxylic acid as a ligand for the Cu-catalyzed reactions of primary anilines with aryl halides [J].

Altman, Ryan A. ;

Anderson, Kevin W. ;

Buchwald, Stephen L. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (13) :5167-5169

[3] The copper-catalyzed N-arylation of indoles [J].

Antilla, JC ;

Klapars, A ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) :11684-11688

[4] THE CHLORINATION OF INDOLES BY COPPER(II) CHLORIDE [J].

BALOGHHERGOVICH, E ;

SPEIER, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (12) :2305-2308

[5] Total synthesis of marine natural products without using protecting groups [J].

Baran, Phil S. ;

Maimone, Thomas J. ;

Richter, Jeremy M. .

NATURE, 2007, 446 (7134) :404-408

[6] Total synthesis of (±)-chartelline C [J].

Baran, Phil S. ;

Shenvi, Ryan A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (43) :14028-14029

[7] A remarkable ring contraction en route to the chartelline alkaloids [J].

Baran, PS ;

Shenvi, RA ;

Mitsos, CA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (24) :3714-3717

[8] Catalytic Oxyamidation of Indoles [J].

Beaumont, Stephane ;

Pons, Valerie ;

Retailleau, Pascal ;

Dodd, Robert H. ;

Dauban, Philippe .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (09) :1634-1637

[9] Studies of the reactions between indole-2,3-diones (isatins) and 2-aminobenzylamine [J].

Bergman, J ;

Engqvist, R ;

Stålhandske, C ;

Wallberg, H .

TETRAHEDRON, 2003, 59 (07) :1033-1048

[10] Reaction progress kinetic analysis: A powerful methodology for mechanistic studies of complex catalytic reactions [J].

Blackmond, DG .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (28) :4302-4320

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