Solid-phase synthesis of tetramic acids

被引：38

作者：

Kulkarni, BA ^{[1
]}

Ganesan, A ^{[1
]}

机构：

[1] Natl Univ Singapore, Inst Mol & Cell Biol, Singapore 117609, Singapore

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 24期

关键词：

combinatorial chemistry; solid-phase synthesis; pyrrolidinones; condensations;

D O I：

10.1016/S0040-4039(98)00703-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Upon treatment with base, N-acylated alpha-amino acids loaded on Wang resin undergo cyclative Claisen-type condensation to release the tetramic acid in high yield and purity. The use of tetrabutylammonium hydroxide as base simplifies product purification, as it can be scavenged by acidic Amberlyst A-15 ion exchange resin. The diversity of the tetramic acids can be further increased by reductive alkylation of the starting amino acid. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4369 / 4372

页数：4

共 17 条

[1]

Balkenhohl F, 1996, ANGEW CHEM INT EDIT, V35, P2289

[2] A GENERAL AND EXPEDIENT METHOD FOR THE SOLID-PHASE SYNTHESIS OF 1,4-BENZODIAZEPINE DERIVATIVES [J].

BUNIN, BA ;

ELLMAN, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) :10997-10998

[3] UNIDIRECTIONAL DIECKMANN CYCLIZATIONS ON A SOLID-PHASE AND IN SOLUTION [J].

CROWLEY, JI ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (16) :3215-3227

[4]

CROWLEY JI, 1970, J AM CHEM SOC, V92, P6363

[5] Non-acidic cleavage of wang-derived ethers from solid support: Utilization of a mixed-bed scavenger for DDQ [J].

Deegan, TL ;

Gooding, OW ;

Baudart, S ;

Porco, JA .

TETRAHEDRON LETTERS, 1997, 38 (28) :4973-4976

[6] DIVERSOMERS - AN APPROACH TO NONPEPTIDE, NONOLIGOMERIC CHEMICAL DIVERSITY [J].

DEWITT, SH ;

KIELY, JS ;

STANKOVIC, CJ ;

SCHROEDER, MC ;

CODY, DMR ;

PAVIA, MR .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (15) :6909-6913

[7] HISTORY OF COMBINATORIAL CHEMISTRY [J].

FURKA, A .

DRUG DEVELOPMENT RESEARCH, 1995, 36 (01) :1-12

[8] Solid-phase organic reactions .2. A review of the literature Nov 95 Nov 96. [J].

Hermkens, PHH ;

Ottenheijm, HCJ ;

Rees, DC .

TETRAHEDRON, 1997, 53 (16) :5643-5678

[9] Ion-exchange resins for combinatorial synthesis: 2,4-pyrrolidinediones by Dieckmann condensation [J].

Kulkarni, BA ;

Ganesan, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (22) :2454-2455

[10] The ''one-bead-one-compound'' combinatorial library method [J].

Lam, KS ;

Lebl, M ;

Krchnak, V .

CHEMICAL REVIEWS, 1997, 97 (02) :411-448

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