ENANTIOSELECTIVE PRODUCTION OF HOMOCHIRAL (+)-(1R,2S,3S,4S)-BICYCLO(2.2.1)HEPTANE-2,3-DICARBOXYLIC AND (-)-(1S,2R,3R,4R)-BICYCLO(2.2.1)HEPTANE-2,3-DICARBOXYLIC ACID, 2-METHYL ESTERS - FORMAL SYNTHESIS OF THE TXA2 ANTAGONIST S-1452

被引：10

作者：

CASAS, R ^{[1
]}

ORTUNO, RM ^{[1
]}

机构：

[1] UNIV AUTONOMA BARCELONA,DEPT QUIM,E-08193 BARCELONA,SPAIN

来源：

TETRAHEDRON-ASYMMETRY | 1992年 / 3卷 / 09期

关键词：

D O I：

10.1016/S0957-4166(00)82106-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Both enantiomers of the title half ester have been synthesized from D-mannitol as single chiral precursor. The dextro-enantiomer is the key intermediate in the synthesis of the TXA2 antagonistic drug S-1452.

引用

页码：1205 / 1212

页数：8

共 13 条

[1] DIELS-ALDER CYCLO-ADDITIONS OF CHIRAL BUTENOLIDES WITH CYCLOPENTADIENE - ENDO EXO SELECTIVITY [J].

BATLLORI, R ;

FONT, J ;

MONSALVATJE, M ;

ORTUNO, RM ;

SANCHEZFERRANDO, F .

TETRAHEDRON, 1989, 45 (06) :1833-1838

[2]

CARLSEN HJ, 1981, J ORG CHEM, V43, P2981

[3] DIASTEREOFACIAL SELECTIVITY IN UNCATALYZED DIELS-ALDER CYCLOADDITIONS INVOLVING ALPHA, BETA-UNSATURATED ESTERS AND LACTONES WITH STEREOGENIC CENTERS CONTAINING OXYGEN FUNCTIONALITIES [J].

CASAS, R ;

PARELLA, T ;

BRANCHADELL, V ;

OLIVA, A ;

ORTUNO, RM ;

GUINGANT, A .

TETRAHEDRON, 1992, 48 (13) :2659-2680

[4] LEWIS ACID-CATALYZED DIELS-ALDER ADDITIONS OF CYCLOPENTADIENE TO METHYL (E)-(S)-4,5-DI-O-ISOPROPYLIDENEPENT-2-ENOATES AND (Z)-(S)-4,5-DI-O-ISOPROPYLIDENEPENT-2-ENOATES - RATE AND STEREOSELECTIVITY [J].

CHEN, ZY ;

ORTUNO, RM .

TETRAHEDRON-ASYMMETRY, 1992, 3 (05) :621-628

[5]

COREY EJ, 1979, TETRAHEDRON LETT, P399

[6] THE SYNTHESIS OF POTENT THROMBOXANE-A2/PROSTAGLANDIN ENDOPEROXIDE RECEPTOR ANTAGONIST [J].

HAMANAKA, N ;

SEKO, T ;

MIYAZAKI, T ;

NAKA, M ;

FURUTA, K ;

YAMAMOTO, H .

TETRAHEDRON LETTERS, 1989, 30 (18) :2399-2402

[7]

HELMCHEN G, 1986, MODERN SYNTHETIC MET, V4

[8] ORGANOPALLADIUM APPROACHES TO PROSTAGLANDINS .7. SYNTHESIS OF PROSTAGLANDIN ENDOPEROXIDE ANALOGS BY VINYLPALLADATION OF NORBORNENE [J].

LAROCK, RC ;

HSU, MH ;

NARAYANAN, K .

TETRAHEDRON, 1987, 43 (13) :2891-2896

[9]

MANN J, 1987, J CHEM RES-S, P369

[10] ENANTIOSELECTIVE SYNTHESIS OF S-1452, AN ORALLY ACTIVE POTENT THROMBOXANE-A2 RECEPTOR ANTAGONIST [J].

OHTANI, M ;

MATSUURA, T ;

WATANABE, F ;

NARISADA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) :2122-2127

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