Syntheses of cystothiazole A and its stereoisomers: importance of stereochemistry for antifungal activity

被引：15

作者：

Ojika, M ^{[1
]}

Watanabe, T ^{[1
]}

Qi, JH ^{[1
]}

Tanino, T ^{[1
]}

Sakagami, Y ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Bioagr Sci, Chikusa Ku, Nagoya, Aichi 4648601, Japan

来源：

TETRAHEDRON | 2004年 / 60卷 / 01期

基金：

日本学术振兴会;

关键词：

cystothiazole A; stereoisomers; antifungal;

D O I：

10.1016/j.tet.2003.10.078

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantiocontrolled total syntheses of all the stereoisomers of a myxobacterial antibiotic, cystothiazole A, are described. The natural syn stereochemistry at the C4-C5 position was controlled by the asymmetric Evans aldol process, whereas the anti relationship was introduced by a modified Evans aldol methodology. Starting with a known aldehyde, the common substrate of the aldol reactions, cystothiazole A and its three stereoisomers were synthesized in 9 steps. All three stereoisomers did not show antifungal activity even at a dosage 2500-fold that of cystothiazole A. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：187 / 194

页数：8

共 22 条

[1]

Bach T, 2002, CHEM-EUR J, V8, P5585, DOI 10.1002/1521-3765(20021216)8:24<5585::AID-CHEM5585>3.0.CO

[2]

2-1

[3]

Bach T, 2001, ANGEW CHEM INT EDIT, V40, P3184, DOI 10.1002/1521-3773(20010903)40:17<3184::AID-ANIE3184>3.0.CO

[4]

2-7

[5] Formal total syntheses of Myxothiazols by three different approaches starting from benzyloxyacetaldehyde [J].

Backhaus, D .

TETRAHEDRON LETTERS, 2000, 41 (13) :2087-2090

[6]

Böhlendorf B, 1999, EUR J ORG CHEM, V1999, P2601

[7] ACYCLIC STEREOSELECTION .48. REVERSAL OF STEREOCHEMISTRY IN THE ALDOL REACTIONS OF A CHIRAL BORON ENOLATE [J].

DANDA, H ;

HANSEN, MM ;

HEATHCOCK, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :173-181

[8] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

BARTROLI, J ;

SHIH, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129

[9] MYXOTHIAZOL, AN ANTIBIOTIC FROM MYXOCOCCUS-FULVUS (MYXOBACTERALES) .1. CULTIVATION, ISOLATION, PHYSICOCHEMICAL AND BIOLOGICAL PROPERTIES [J].

GERTH, K ;

IRSCHIK, H ;

REICHENBACH, H ;

TROWITZSCH, W .

JOURNAL OF ANTIBIOTICS, 1980, 33 (12) :1474-1479

[10] New total synthesis of (+)-cytothiazole A based on palladium-catalyzed cyclization-methoxycarbonylation [J].

Kato, K ;

Sasaki, T ;

Takayama, H ;

Akita, H .

TETRAHEDRON, 2003, 59 (15) :2679-2685

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