Enantioselective synthesis of 2-[(3-ethyl-4-piperidyl)methyl]indoles from a phenylglycinol-derived lactam:: formal synthesis of Strychnos alkaloids

被引：9

作者：

Amat, Mercedes ^{[1
]}

Llor, Nuria ^{[1
]}

Checa, Begona ^{[1
]}

Perez, Maria ^{[1
]}

Bosch, Joan ^{[1
]}

机构：

[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 38期

关键词：

phenylglycinol; Strychnos alkaloids; piperidines; indoles; oxazolopiperidone lactams;

D O I：

10.1016/j.tetlet.2007.07.079

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A diastereodivergent synthesis of enantiopure cis- and traiis-2-[(3-ethyl-4-piperidyl)methyl]indole (cis-1b and trans-1b) from a common phenylglycino]-derived oxazolopiperidone lactam 3 is reported. The key step is a stereocontrolled conjugate addition, either under kinetic or thermodynamic control, of the dilithium salt of 2-(2-indolyl)-1,3-dithiane to unsaturated lactam 3. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：6722 / 6725

页数：4

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