Asymmetric synthesis of the chlorocyclopropane containing callipeltoside A side chain

被引:55
作者
Evans, DA [1 ]
Burch, JD [1 ]
机构
[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
关键词
D O I
10.1021/ol0155182
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The callipeltoside A chlorocyclopropyl-containing dienyne side chain has been synthesized in nine steps and 33% overall yield from commercially available 1,2,5,6-O-dicyclohexylidene-D-mannitol. The key steps in the synthesis are a highly diastereoselective cyclopropanation of a vinyl chloride allylic ether and a Suzuki cross-coupling to complete the carbon framework.
引用
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页码:503 / 505
页数:3
相关论文
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[21]   Callipeltoside A: A cytotoxic aminodeoxy sugar-containing macrolide of a new type from the marine Lithistida sponge Callipelta sp [J].
Zampella, A ;
DAuria, MV ;
Minale, L ;
Debitus, C ;
Roussakis, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (45) :11085-11088