The naturally occurring ketene acetal benesudon: Total synthesis and assignment of relative and absolute stereochemistry

被引：5
|
作者：
Clive, Derrick L. J. [1 ]
Minaruzzaman [1 ]
Yang, Haikang [1 ]
机构：
[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 17期
基金：
加拿大自然科学与工程研究理事会;
关键词：
D O I：
10.1021/jo801028y
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The densely functionalized ketene acetal benesudon, which is a bioactive fungal metabolite, was synthesized from D-glucose by a route involving radical cyclization to form the five-membered ring, and oxidative decarboxylation to generate the key central double bond. The originally suggested stereochemistry for the quaternary center C(5) must be revised, as both C(5) epimers were prepared and a comparison with an authentic sample was made. The absolute configuration of benesudon is 4S,5R,6S.
引用
收藏
页码：6743 / 6752
页数：10
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