Towards the Total Synthesis of Pl-3: Preparation of the Eastern Fragment through a Diastereoselective SmI2-Mediated Reformatsky Reaction

被引：17
|
作者：
Fuerst, Rita [1 ]
Lentsch, Christoph [1 ]
Rinner, Uwe [1 ]
机构：
[1] Univ Vienna, Dept Organ Chem, A-1090 Vienna, Austria
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 12期
关键词：
Natural products; Terpenoids; Samarium; Diastereoselectivity; Multidrug resistance; RESISTANCE REVERSING ACTIVITY; JATROPHANE DITERPENES; MOUSE LYMPHOMA; DERIVATIVES; INHIBITORS; PLANTS;
D O I：
10.1002/ejoc.201300148
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The jatrophane diterpene Pl-3, isolated in 2003 from Euphorbia platyphyllos, is a structurally complex natural product with highly promising biological properties that include pronounced antiproliferative activity and the inhibition of the efflux-pump activity of multidrug resistance p-glycoprotein. Herein, the synthesis of the eastern fragment of Pl-3 is outlined. The target compound is synthesized in nine synthetic operations in good overall yield, starting from readily available D-ribose. The key step in the preparation of the eastern part of Pl-3 is a diastereoselective SmI2-mediated Reformatsky reaction. The proposed route is highly flexible and could also be applied to the synthesis of structurally related jatrophane diterpenes.
引用
收藏
页码：2293 / 2297
页数：5
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