Synthesis of the Stenine Ring System from Pyrrole

被引：36

作者：

Bates, Roderick W. ^{[1
]}

Sridhar, S. ^{[1
]}

机构：

[1] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 12期

关键词：

RUTHENIUM-CATALYZED CYCLOCARBONYLATION; STEMONA ALKALOID (-)-STENINE; ENYNE METATHESIS REACTION; ALLENYL ALCOHOLS; 3-SUBSTITUTED PYRROLES; SELECTIVE SYNTHESIS; DIMETHYL-SULFOXIDE; LACTONES; (-)-STEMOAMIDE; (+/-)-STENINE;

D O I：

10.1021/jo200699k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：5026 / 5035

页数：10

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