Convenient synthesis of novel macrocyclic urethanes: Alkoxycarbonylation of amines and ring-closing metathesis strategy

被引：21

作者：

Ghosh, AK ^{[1
]}

Hussain, KA ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 14期

关键词：

D O I：

10.1016/S0040-4039(98)00153-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkoxycarbonylation of amines followed by ring-closing metathesis of the resulting dienes with Grubbs catalyst (25-50 mol%) provided convenient access to 14-16 membered macrocyclic urethanes in very good yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：1881 / 1884

页数：4

相关论文

共 22 条

[1] Total synthesis of (-)-epothilone A [J].

Balog, A ;

Meng, DF ;

Kamenecka, T ;

Bertinato, P ;

Su, DS ;

Sorensen, EJ ;

Danishefsky, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (23-24) :2801-2803

[2] POLYMERIZATION OF FUNCTIONALIZED NORBORNENES EMPLOYING MO(CH-T-BU)(NAR)(O-T-BU)2 AS THE INITIATOR [J].

BAZAN, GC ;

SCHROCK, RR ;

CHO, HN ;

GIBSON, VC .

MACROMOLECULES, 1991, 24 (16) :4495-4502

[3] Asymmetric aldol-ring-closing metathesis strategy for the enantioselective construction of six- to nine-membered oxygen heterocycles [J].

Crimmins, MT ;

Choy, AL .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) :7548-7549

[4] CATALYTIC RING-CLOSING METATHESIS OF FUNCTIONALIZED DIENES BY A RUTHENIUM CARBENE COMPLEX [J].

FU, GC ;

NGUYEN, ST ;

GRUBBS, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9856-9857

[5] Total syntheses of (+)-ricinelaidic acid lactone and of (-)-gloeosporone based on transition-metal-catalyzed C-C bond formations [J].

Furstner, A ;

Langemann, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (39) :9130-9136

[6] N,N'-DISUCCINIMIDYL CARBONATE - A USEFUL REAGENT FOR ALKOXYCARBONYLATION OF AMINES [J].

GHOSH, AK ;

DUONG, TT ;

MCKEE, SP ;

THOMPSON, WJ .

TETRAHEDRON LETTERS, 1992, 33 (20) :2781-2784

[7] STRUCTURE-BASED DESIGN OF HIV-1 PROTEASE INHIBITORS - REPLACEMENT OF 2 AMIDES AND A 10-PI-AROMATIC SYSTEM BY A FUSED BIS-TETRAHYDROFURAN [J].

GHOSH, AK ;

THOMPSON, WJ ;

FITZGERALD, PMD ;

CULBERSON, JC ;

AXEL, MG ;

MCKEE, SP ;

HUFF, JR ;

ANDERSON, PS .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (16) :2506-2508

[8] THE DEVELOPMENT OF CYCLIC SULFOLANES AS NOVEL AND HIGH-AFFINITY P(2) LIGANDS FOR HIV-1 PROTEASE INHIBITORS [J].

GHOSH, AK ;

LEE, HY ;

THOMPSON, WJ ;

CULBERSON, C ;

HOLLOWAY, MK ;

MCKEE, SP ;

MUNSON, PM ;

DUONG, TT ;

SMITH, AM ;

DARKE, PL ;

ZUGAY, JA ;

EMINI, EA ;

SCHLEIF, WA ;

HUFF, JR ;

ANDERSON, PS .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (08) :1177-1188

[9] Nonpeptidal P-2 ligands for HIV protease inhibitors: Structure-based design, synthesis, and biological evaluation [J].

Ghosh, AK ;

Kincaid, JF ;

Walters, DE ;

Chen, Y ;

Chaudhuri, NC ;

Thompson, WJ ;

Culberson, C ;

Fitzgerald, PMD ;

Lee, HY ;

McKee, SP ;

Munson, PM ;

Duong, TT ;

Darke, PL ;

Zugay, JA ;

Schleif, WA ;

Axel, MG ;

Lin, J ;

Huff, JR .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (17) :3278-3290

[10] DI(2-PYRIDYL) CARBONATE PROMOTED ALKOXYCARBONYLATION OF AMINES - A CONVENIENT SYNTHESIS OF FUNCTIONALIZED CARBAMATES [J].

GHOSH, AK ;

DUONG, TT ;

MCKEE, SP .

TETRAHEDRON LETTERS, 1991, 32 (34) :4251-4254