An unprecedented asymmetric Nazarov cyclization for the synthesis of nonracemic indanes as endothelin receptor antagonists

被引：42

作者：

Pridgen, LN

Huang, K

Shilcrat, S

Tickner-Eldridge, A

DeBrosse, C

Haltiwanger, RC

机构：

[1] SmithKline Beecham Pharmaceut, Dept Synthet Chem, King Of Prussia, PA 19406 USA

[2] SmithKline Beecham Pharmaceut, Dept Analyt Sci, King Of Prussia, PA 19406 USA

[3] SmithKline Beecham Pharmaceut, Dept Phys & Struct Chem, King Of Prussia, PA 19406 USA

来源：

SYNLETT | 1999年 / 10期

关键词：

asymmetric Nazarov cyclization; 1,5-asymmetric induction; endothelin receptor antagonists; indanes;

D O I：

10.1055/s-1999-2912

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric synthesis of the novel nonracemic endothelin receptor antagonists, SE 209670 (la) and SE 217242 (1b) is described which utilizes an unprecedented asymmetric Nazarov-type ring closure of the alkylidene-l,3-carbonyl compounds. Excellent 1,5-induction is observed which establishes the required S configuration at the C-3 carbon of an indane skeleton.

引用

页码：1612 / 1614

页数：3

共 16 条

[11] An optimized palladium catalyzed cross-coupling of nonracemic trifluoromethylsulfonyl and fluorosulfonyl enol ethers to arylboronic acids [J].