C-GLYCOSYLANTHRAQUINONE SYNTHESIS - TOTAL SYNTHESIS OF VINEOMYCINONE-B2 METHYL-ESTER

被引：102
作者：
TIUS, MA
GOMEZGALENO, J
GU, XQ
ZAIDI, JH
机构：
[1] Department of Chemistry, University of Hawaii, Honolulu, Hawaii 96822
[2] Federal Government College, Department of Chemistry, H8, Islamabad
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1991年 / 113卷 / 15期
关键词：
D O I：
10.1021/ja00015a035
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A synthesis of substituted anthraquinones has been developed. Commercially available anthrarufin and 1,8-dihydroxyanthraquinone were converted to the corresponding (methoxymethoxy)anthracenes. Directed metalation followed by stannylation produced stable intermediates that were either alkylated, arylated, acylated, and/or C-glycosylated. The value of this new methodology was demonstrated by the triply convergent total synthesis of vineomycinone B2 methyl ester, a representative C-glycosylanthraquinone antibiotic.
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页码：5775 / 5783
页数：9
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