Synthesis of the Stenine Ring System from Pyrrole
Synthesis of the Stenine Ring System from Pyrrole
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DOI：
10.1021/jo200699k
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发表时间：
2011-06-17
影响因子：
3.6
通讯作者：
Sridhar, S.
中科院分区：
文献类型：
--
作者：
Bates, Roderick W.;Sridhar, S.
The skeleton of the stemona alkaloid, stenine, has been synthesized starting from pyrrole, employing an asymmetric organocatalyzed cyclization, Sonogashira coupling, a diastereoselective intramolecular propargylic Barbier reaction, cyclocarbonylation, and diastereoselective alkene reduction. Modulation of the electron-rich nature of the pyrrole nucleus by employing an a-trifluoroacetyl group is essential. The alpha-trifluoroacetyl group may be rapidly removed under carefully defined, mild conditions.
