A PRACTICAL ASYMMETRIC-SYNTHESIS OF LTD(4) ANTAGONIST

被引：53

作者：

SHINKAI, I

KING, AO

LARSEN, RD

机构：

[1] Merck Research Laboratories, Process Research & Development, Rahway, New Jersey

来源：

PURE AND APPLIED CHEMISTRY | 1994年 / 66卷 / 07期

关键词：

D O I：

10.1351/pac199466071551

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The asymmetric synthesis of L-699,392, a leukotriene antagonist, is reported. The main framework of the molecule is formed via a Heck reaction. The introduction of the asymmetric center was accomplished by the chiral reduction of prochiral ketone using B-chlorodiidopinocampheylborane. A very high asymmetric amplification was observed in which 95% ee product can be obtained from 70% optically pure alpha-pinene. A new reagent, which is prepared in situ from methylmagnesium chloride and lithium-hexamethyldisilazide, is used to convert the methyl ester to the methyl ketone in one step with essentially no impurities formed under the reaction conditions.

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页码：1551 / 1556

页数：6

相关论文

共 11 条

[1] CHIRAL SYNTHESIS VIA ORGANOBORANES .22. SELECTIVE REDUCTIONS .44. THE EFFECT OF THE STERIC REQUIREMENTS OF THE ALKYL SUBSTITUENT IN ISOPINOCAMPHEYLALKYLCHLOROBORANES FOR THE ASYMMETRIC REDUCTION OF REPRESENTATIVE KETONES [J].

BROWN, HC ;

SREBNIK, M ;

RAMACHANDRAN, PV .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1577-1583

[2] HYDROBORATION .52. MONOHALOBORANE METHYL SULFIDE ADDUCTS AS NEW REAGENTS FOR THE HYDROBORATION OF ALKENES - CONVENIENT SYNTHESIS OF DIALKYLHALOBORANES AND THEIR DERIVATIVES FOR ORGANIC-SYNTHESIS [J].

BROWN, HC ;

RAVINDRAN, N ;

KULKARNI, SU .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (14) :2417-2422

[3]

CABRI W, 1992, J ORG CHEM, V57, P5358

[4] HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553

[5] LIPASE-CATALYZED ASYMMETRIC HYDROLYSIS OF ESTERS HAVING REMOTE CHIRAL PROCHIRAL CENTERS [J].

HUGHES, DL ;

BERGAN, JJ ;

AMATO, JS ;

BHUPATHY, M ;

LEAZER, JL ;

MCNAMARA, JM ;

SIDLER, DR ;

REIDER, PJ ;

GRABOWSKI, EJJ .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) :6252-6259

[6] AN EFFICIENT SYNTHESIS OF LTD4 ANTAGONIST L-699,392 [J].

KING, AO ;

CORLEY, EG ;

ANDERSON, RK ;

LARSEN, RD ;

VERHOEVEN, TR ;

REIDER, PJ ;

XIANG, YB ;

BELLEY, M ;

LEBLANC, Y ;

LABELLE, M ;

PRASIT, P ;

ZAMBONI, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (14) :3731-3735

[7] A PRACTICAL ENANTIOSELECTIVE SYNTHESIS OF ALPHA,ALPHA-DIARYL-2-PYRROLIDINEMETHANOL - PREPARATION AND CHEMISTRY OF THE CORRESPONDING OXAZABOROLIDINES [J].

MATHRE, DJ ;

JONES, TK ;

XAVIER, LC ;

BLACKLOCK, TJ ;

REAMER, RA ;

MOHAN, JJ ;

JONES, ETT ;

HOOGSTEEN, K ;

BAUM, MW ;

GRABOWSKI, EJJ .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :751-762

[8] SYNTHESIS OF UNSYMMETRICAL DITHIOACETALS - AN EFFICIENT SYNTHESIS OF A NOVEL LTD4 ANTAGONIST, L-660,711 [J].

MCNAMARA, JM ;

LEAZER, JL ;

BHUPATHY, M ;

AMATO, JS ;

REAMER, RA ;

REIDER, PJ ;

GRABOWSKI, EJJ .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (15) :3718-3721

[9] A PRACTICAL, ONE-POT PREPARATION OF DIISOPINOCAMPHEYLCHLOROBORANE [J].

SIMPSON, P ;

TSCHAEN, D ;

VERHOEVEN, TR .

SYNTHETIC COMMUNICATIONS, 1991, 21 (15-16) :1705-1714

[10]

WEINREB SM, 1981, TETRAHEDRON LETT, V22, P3815