Stereoselective Approach to the Racemic Oxatetracyclic Core of Platensimycin

Stereoselective Approach to the Racemic Oxatetracyclic Core of Platensimycin
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DOI:
10.1021/jo302813y
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发表时间:
2013-03-15
影响因子:
3.6
通讯作者:
Kuwahara, Shigefumi
Kuwahara, Shigefumi
中科院分区:
化学2区
文献类型:
--
作者:
Horii, Sakuya;Torihata, Munefumi;Kuwahara, Shigefumi

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以已知的双环环氧内酯为原料,通过11步反应,通过Diels-Alder环化反应构建了具有完全区域和立体选择性的顺式十碳烯酮结构模体,并进行了闭环歧化反应以建立其完整的碳骨架,从而完成了外消旋氧四环中心的高度立体选择性合成。
A highly stereoselective synthesis of the racemic oxatetracyclic core of platensimycin has been accomplished from a known bicyclic epoxy lactone by an 11-step sequence that involves a Diels-Alder cycicoacldition to construct its cis-decalenone structural motif with complete regio- and stereoselectivity and a ring-closing metathesis to establish its whole carbon framework.