Synthetic studies of thiazoline and thiazolidine-containing natural products - 2. Total synthesis of the antimycoplasma antibiotic micacocidin

被引：28

作者：

Ino, A ^{[1
]}

Hasegawa, Y ^{[1
]}

Murabayashi, A ^{[1
]}

机构：

[1] Shionogi & Co Ltd, Aburahi Labs, Shiga 5203423, Japan

来源：

TETRAHEDRON | 1999年 / 55卷 / 34期

关键词：

antibiotics; thiazolines; thiazolidines; chelation;

D O I：

10.1016/S0040-4020(99)00583-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of the right half of micacocodin (segment B) and subsequent completion of total synthesis of the antimycoplasma antibiotic micacocidin is described. The desired S-configuration at C-14 secondary carbinol was obtained by stereoselective reduction of the preceding ketone in accordance with the Cram rule. Condensation of two labile segments, A and B, was achieved in the presence of potassium acetate. The chiral center at C-10 was finally isomerized to the natural configuration through formation of the Zn complex. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：10283 / 10294

页数：12

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