CHIRAL SYNTHESIS OF POLYKETIDE DERIVED NATURAL-PRODUCTS .27. STEREOSELECTIVE SYNTHESIS OF ERYTHRONOLIDE-A VIA AN EXTREMELY EFFICIENT MACROLACTONIZATION BY THE MODIFIED YAMAGUCHI METHOD

被引:147
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
关键词
D O I
10.1021/jo00288a004
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
: The seco-acid derivative 7, which has the 9,11-and 3,5-diols protected as the mesityl- and 3,4-dimeth-oxypheny- (DMP) acetals, respectively, was stereoselectively synthesized from D-glucose and converted to Yam-aguchi's mixed anhydride, which was treated with a high concentration of DMAP at room temperature to rapidly give the 14-membered lactone in 98% yield. Removal of the protecting groups gave 9-dihydroerythronolide A. © 1990, American Chemical Society. All rights reserved.
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页码:7 / 9
页数:3
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