Enantioselective synthesis of a 5-LO inhibiting hydroxyurea. Construction of the dihydro-benzofuran nucleus by tandem nucleophilic addition and intramolecular cyclization.

被引：10

作者：

Flisak, JR ^{[1
]}

Lantos, I ^{[1
]}

Liu, L ^{[1
]}

Matsuoka, RT ^{[1
]}

Mendelson, WL ^{[1
]}

Tucker, LM ^{[1
]}

Villani, AJ ^{[1
]}

Zhang, WY ^{[1
]}

机构：

[1] SMITHKLINE BEECHAM PHARMACEUT,DEPT SYNTHET CHEM,KING OF PRUSSIA,PA 19406

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 27期

关键词：

D O I：

10.1016/0040-4039(96)00922-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective synthesis of a 5-LO inhibiting chiral hydroxyurea is described based on the nucleophilic addition of dimethylsulfoxonium ylide to a nitrone bearing a mannose-derived chiral auxiliary. The dihydrobenzofuran skeleton is then constructed by a spontaneous cyclization of the initial adduct, thus completing a tandem nucleophilic addition-cyclization protocol. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：4639 / 4642

页数：4

共 13 条

[1] ADDITION OF ORGANOMETALLIC REAGENTS TO N-GLYCOSYL NITRONES - ENANTIOSELECTIVE SYNTHESES OF (+)-(R)-ZILEUTON AND (-)-(S)-ZILEUTON [J].

BASHA, A ;

HENRY, R ;

MCLAUGHLIN, MA ;

RATAJCZYK, JD ;

WITTENBERGER, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (20) :6103-6106

[2] DIASTEREOSELECTIVITY OF ORGANOMETALLIC ADDITIONS TO NITRONES BEARING STEREOGENIC N-SUBSTITUENTS [J].

CHANG, ZY ;

COATES, RM .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3464-3474

[3] DIMETHYLSULFOXONIUM METHYLIDE [J].

COREY, EJ ;

CHAYKOVSKY, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (05) :867-&

[4] DIMETHYLOXOSULFONIUM METHYLIDE ((CH3)2SOCH2) AND DIMETHYLSULFONIUM METHYLIDE ((CH3)2SCH2) FORMATION AND APPLICATION TO ORGANIC SYNTHESIS [J].

COREY, EJ ;

CHAYKOVSKY, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) :1353-+

[5]

GARIGIPATI RS, 1993, TETRAHEDRON LETT, V35, P5537

[6] 25 YEARS OF DIMETHYLSULFOXONIUM METHYLIDE (COREYS REAGENT) [J].

GOLOLOBOV, YG ;

NESMEYANOV, AN ;

LYSENKO, VP ;

BOLDESKUL, IE .

TETRAHEDRON, 1987, 43 (12) :2609-2651

[7]

HU X, 1992, 204 NAT M AM CHEM SO

[8]

Johnson C. R., 1985, ALDRICHIM ACTA, V18, P3

[9] YLIDES FROM SALTS OF SULFOXIMINES [J].

JOHNSON, CR ;

JANIGA, ER ;

HAAKE, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (14) :3890-&

[10] PREPARATION AND SYNTHETIC APPLICATIONS OF (DIMETHYLAMINO)PHENYLOXOSULFONIUM METHYLIDE [J].

JOHNSON, CR ;

HAAKE, M ;

SCHROECK, CW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (22) :6594-&

← 1 2 →