Total synthesis of LFA-1 antagonist BIRT-377 via organocatalytic asymmetric construction of a quaternary stereocenter

被引：148

作者：

Chowdari, NS

Barbas, CF

机构：

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

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

[3] Scripps Res Inst, Dept Biol Mol, La Jolla, CA 92037 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 05期

关键词：

D O I：

10.1021/ol047368b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic route for enantioselective total synthesis of cell adhesion inhibitor BIRT-377 is described. The quaternary stereocenter was constructed through L-proline-derived, tetrazole-catalyzed direct asymmetric alpha-amination of 3-(4-bromophenyl)-2-methylpropanaI with dibenzyl azodicarboxylate. In the course of these studies, a one-pot trifluoro acetylation/selective benzyloxycarbonyl deprotection method was developed.

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页码：867 / 870

页数：4

相关论文

共 71 条

[31] General and practical catalytic enantioselective Strecker reaction of ketoimines: significant improvement through catalyst tuning by protic additives [J].

Kato, N ;

Suzuki, M ;

Kanai, M ;

Shibasaki, M .

TETRAHEDRON LETTERS, 2004, 45 (15) :3147-3151

[32] HIGHLY CHEMOSELECTIVE PALLADIUM-CATALYZED CONJUGATE REDUCTION OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS WITH SILICON HYDRIDES AND ZINC-CHLORIDE COCATALYST [J].

KEINAN, E ;

GREENSPOON, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (23) :7314-7325

[33] Discovery of new peptide-based catalysts for the direct asymmetric aldol reaction [J].

Kofoed, J ;

Nielsen, J ;

Reymond, JL .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (15) :2445-2447

[34] Direct preparation of monoarylidene derivatives of aldehydes and enolizable ketones with DIMCARB [J].

Kreher, UP ;

Rosamilia, AE ;

Raston, CL ;

Scott, JL ;

Strauss, CR .

ORGANIC LETTERS, 2003, 5 (17) :3107-3110

[35] Direct L-proline-catalyzed asymmetric α-amination of ketones [J].

Kumaragurubaran, N ;

Juhl, K ;

Zhuang, W ;

Bogevig, A ;

Jorgensen, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (22) :6254-6255

[36] Catalytic asymmetric allylation of prochiral nucleophiles, α-acetamido-β-ketoesters [J].

Kuwano, R ;

Ito, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) :3236-3237

[37]

Lee SH, 2001, B KOREAN CHEM SOC, V22, P551

[38] Proline-catalyzed direct asymmetric aldol reactions [J].

List, B ;

Lerner, RA ;

Barbas, CF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (10) :2395-2396

[39] Direct catalytic asymmetric α-amination of aldehydes [J].

List, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (20) :5656-5657

[40] The proline-catalyzed direct asymmetric three-component Mannich reaction: Scope, optimization, and application to the highly enantioselective synthesis of 1,2-amino alcohols [J].

List, B ;

Pojarliev, P ;

Biller, WT ;

Martin, HJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (05) :827-833

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