Towards the synthesis of epothilone A: Enantioselective preparation of the thiazole sidechain and macrocyclic ring closure

被引：48

作者：

Taylor, RE

Haley, JD

机构：

[1] Dept. of Chemistry and Biochemistry, University of Notre Dame, Notre Dame

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 12期

关键词：

D O I：

10.1016/S0040-4039(97)00285-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthetic approach to a new class of microtubule-stabilizing natural products is described which employs a macrocyclic olefination strategy to cyclize the 16-membered lactone ring. The C13-C19 thiazole subunit of epothilone A and B is prepared in high enantioselectivity using a catalytic asymmetric allylation reaction. (C) 1997 Elsevier Science Ltd.

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页码：2061 / 2064

页数：4

相关论文

共 19 条

[1]

[Anonymous], [No title captured], Patent No. [DE 4138042, 4138042]

[2] 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

[3] Studies toward a synthesis of epothilone A: Stereocontrolled assembly of the acyl region and models for macrocyclization [J].

Bertinato, P ;

Sorensen, EJ ;

Meng, DF ;

Danishefsky, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :8000-8001

[4]

BOLLAG DM, 1995, CANCER RES, V55, P2325

[5] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[6]

GERTH K, 1996, J ANTIBIOT, V49, P960

[7] Epothilone A and B - Novel 16-membered macrolides with cytotoxic activity: Isolation, crystal structure, and conformation in solution [J].

Hofle, GH ;

Bedorf, N ;

Steinmetz, H ;

Schomburg, D ;

Gerth, K ;

Reichenbach, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (13-14) :1567-1569

[8] CASCADE CATALYSIS IN SYNTHESIS - AN ENANTIOSELECTIVE ROUTE TO SCH-38516 (AND FLUVIRUCIN-B-1) AGLYCON MACROLACTAM [J].

HOURI, AF ;

XU, ZM ;

COGAN, DA ;

HOVEYDA, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (10) :2943-2944

[9] CATALYTIC ASYMMETRIC ALLYLATION (CAA) REACTIONS .2. A NEW ENANTIOSELECTIVE ALLYLATION PROCEDURE [J].

KECK, GE ;

GERACI, LS .

TETRAHEDRON LETTERS, 1993, 34 (49) :7827-7828

[10] ISOMERIZATION OF INTERNAL TRIPLE BONDS OF ALKYN-1-OLS WITH SODIUM HYDRIDE IN 1,3-DIAMINOPROPANE [J].

MACAULAY, SR .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (04) :734-735