Attempted synthesis of spongidines by a radical cascade terminating onto a pyridine ring

被引:21
作者
Gonzalez, Miguel A. [1 ]
Molina-Navarro, Sonia [1 ]
机构
[1] Univ Valencia, Dept Quim Organ, E-46100 Valencia, Spain
关键词
D O I
10.1021/jo0712401
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Mn(III)-based oxidative free-radical cyclization of an unsaturated beta-keto ester containing a pyridine ring as radical trap has been studied. This intramolecular reaction of nucleophilic carbon-centered radicals with the pyridine ring leads to the stereospecific construction of a tetracyclic compound in which five chiral centers are created in one pot. This synthetic approach represents the first attempt to prepare the anti-inflammatory pyridinium alkaloids spongidine A, B, and D.
引用
收藏
页码:7462 / 7465
页数:4
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