Total syntheses of (±)-cis-trikentrin A and (±)-cis-trikentrin B via electrocyclic ring closures of 2,3-divinylpyrrolines

被引:40
|
作者
Huntley, Raymond J. [1 ]
Funk, Raymond L. [1 ]
机构
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
关键词
D O I
10.1021/ol061259a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convergent and versatile strategy for the diastereoselective syntheses of (+/-)-cis-trikentrin A and B in 10 and 12 steps, respectively, from commercially available N-BOC-2-pyrrolidinone is described. The key step in each of the total syntheses is the construction of the central benzene ring via a facile 6 pi-electrocyclic ring closure of an appropriately substituted 2,3-divinylpyrroline, in turn, readily available by a Stille coupling reaction.
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页码:3403 / 3406
页数:4
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