Stereoselective route to oxetanocin carbocyclic analogues based on a [2+2] photocycloaddition to a chiral 2(5H)-furanone

被引：36
|
作者：
Rustullet, Albert [1 ]
Alibes, Ramon [1 ]
de March, Pedro [1 ]
Figueredo, Marta [1 ]
Font, Josep [1 ]
机构：
[1] Univ Autonoma Barcelona, Dept Quim, E-08193 Bellaterra, Spain
来源：
ORGANIC LETTERS | 2007年 / 9卷 / 15期
关键词：
D O I：
10.1021/ol0710616
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of the trisubstituted cyclobutane 7, which is a suitable precursor for the preparation of oxetanocin carbocyclic analogues, is described. The key step involves a regio- and diastereoselective [2 + 2] photochemical reaction of ketene diethyl acetal with (S)-5-pivaloyloxymethyl-2(5H)-furanone, 3. As an application of this methodology, (-)-cyclobut-A has been prepared from the intermediate 7.
引用
收藏
页码：2827 / 2830
页数：4
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