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

收藏

页码：1612 / 1614

页数：3

相关论文

共 16 条

[1] Highly diastereoselective cycloisomerization of acyclic trienones. The interrupted Nazarov reaction [J].

Bender, JA ;

Blize, AE ;

Browder, CC ;

Giese, S ;

West, FG .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2430-2431

[2] INTRAMOLECULAR RING-CLOSURE OF ALPHA,BETA-UNSATURATED 3-ACYLINDOLES [J].

BERGMAN, J ;

VENEMALM, L .

TETRAHEDRON LETTERS, 1987, 28 (32) :3741-3744

[3] A catalytic enantioselective synthesis of the endothelin receptor antagonists SB-209670 and SB-217242. A base-catalyzed stereospecific formal 1,3-hydrogen transfer of a chiral 3-arylindenol [J].

Clark, WM ;

Tickner-Eldridge, AM ;

Huang, GK ;

Pridgen, LN ;

Olsen, MA ;

Mills, RJ ;

Lantos, I ;

Baine, NH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) :4550-4551

[4]

Denmark S. E., 1991, COMPREHENSIVE ORGANI, V5, P751

[5] 1,3-DIARYLINDAN-2-CARBOXYLIC ACIDS, POTENT AND SELECTIVE NONPEPTIDE ENDOTHELIN RECEPTOR ANTAGONISTS [J].

ELLIOTT, JD ;

LAGO, MA ;

COUSINS, RD ;

GAO, AM ;

LEBER, JD ;

ERHARD, KF ;

NAMBI, P ;

ELSHOURBAGY, NA ;

KUMAR, C ;

LEE, JA ;

BEAN, JW ;

DEBROSSE, CW ;

EGGLESTON, DS ;

BROOKS, DP ;

FEUERSTEIN, G ;

RUFFOLO, RR ;

WEINSTOCK, J ;

GLEASON, JG ;

PEISHOFF, CE ;

OHLSTEIN, EH .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (11) :1553-1557

[6]

Habermas K.L., 1994, ORG REACTIONS, V45, P1

[7]

Ichikawa J, 1998, SYNLETT, P927

[8]

Kajioka T, 1999, SYNTHESIS-STUTTGART, P184

[9] An efficient asymmetric catalytic hydrogenation of 4-aryl coumarins, preparation of a key intermediate in the synthesis of a class of endothelin receptor antagonists [J].

McGuire, MA ;

Shilcrat, SC ;

Sorenson, E .

TETRAHEDRON LETTERS, 1999, 40 (17) :3293-3296

[10]

MILLS RL, UNPUB