CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL-PRODUCTS .31. STEREOSELECTIVE SYNTHESIS OF ERYTHRONOLIDE A BY EXTREMELY EFFICIENT LACTONIZATION BASED ON CONFORMATIONAL ADJUSTMENT AND HIGH ACTIVATION OF SECO-ACID

被引：80

作者：

HIKOTA, M ^{[1
]}

TONE, H ^{[1
]}

HORITA, K ^{[1
]}

YONEMITSU, O ^{[1
]}

机构：

[1] HOKKAIDO UNIV,FAC PHARMACEUT SCI,SAPPORO,HOKKAIDO 060,JAPAN

来源：

TETRAHEDRON | 1990年 / 46卷 / 13-14期

关键词：

D O I：

10.1016/S0040-4020(01)85585-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

C1-C5 sulfone (11) and C7-C15 aldehyde (20), synthesized stereoselectively from D- glucose, were coupled, and the C5 and C6 chiral centers were constructed taking advantage of the MPM (4-methoxybenzyl) type protecting group to give the seco-acid (7), which has 9,11-and 3,5- diols protected as the mesityl- and DMP (3,4-dimethoxyphenyl) acetals, respectively. When Yamaguchi's mixed anhydride of 7 was treated with a high concentration of DMAP at room temperature, a very rapid cyclization occurred and the 14-membered lactone (8) was isolated in almost quantitative yield. Deprotection of 8 readily gave 9-dihydroerythronolide A (2), which was converted to the title compound (1). © 1990.

引用

页码：4613 / 4628

页数：16

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