Aziridine-2-carboxylic acid mediated asymmetric synthesis of D-erythro- and L-threo-sphingosine from a common precursor

被引:77
作者
Davis, FA
Reddy, GV
机构
[1] Department of Chemistry, Temple University, Philadelphia
关键词
D O I
10.1016/0040-4039(96)00827-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Short, two and three step asymmetric syntheses of L-threo- and D-erythro-sphingosine (-)-6a and (-)-9a, respectively, in 58 and 31 percent overall yield were accomplished via the stereo and regioselective ring opening of N-sulfinylaziridine 2-carboxylic acid 4. Copyright (C) 1996 Elsevier Science Ltd.
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页码:4349 / 4352
页数:4
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共 25 条
[1]   IODOCYCLOFUNCTIONALIZATION OF (Z)-1-TRICHLOROACETIMIDOYLOXYALK-2-ENES AND "3-TRICHLOROACETIMIDOYLOXYALK-1-ENES - SYNTHESIS OF (+/-)-ERYTHRO-SPHINGANINE TRIACETATE AND (+/-)-THREO-SPHINGANINE TRIACETATE [J].
BONGINI, A ;
CARDILLO, G ;
ORENA, M ;
SANDRI, S ;
TOMASINI, C .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (08) :1339-1344
[2]   IODOCYCLOFUNCTIONALIZATION OF (E)-1-TRICHLOROACETIMIDOALK-2-ENES - SYNTHESIS OF (+/-)-ERYTHRO-SPHINGANINE TRIACETATE [J].
BONGINI, A ;
CARDILLO, G ;
ORENA, M ;
SANDRI, S ;
TOMASINI, C .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (08) :1345-1349
[3]   BEHAVIOR OF 2-PARA-TOLYLSULFINYL CYCLOHEXANOLS UNDER THE PUMMERER REACTION CONDITIONS [J].
BUENO, AB ;
CARRENO, MC ;
RUANO, JLG ;
RUBIO, A .
TETRAHEDRON-ASYMMETRY, 1992, 3 (02) :251-254
[4]   A NOVEL, EFFICIENT SYNTHESIS OF (+/-)-ERYTHRO-SPHINGOSINE [J].
CARDILLO, G ;
ORENA, M ;
SANDRI, S ;
TOMASINI, C .
TETRAHEDRON, 1986, 42 (03) :917-922
[5]   ASYMMETRIC-SYNTHESIS OF THE ANTIBIOTIC (+)-THIAMPHENICOL USING CIS-N-(P-TOLUENESULFINYL)AZIRIDINE 2-CARBOXYLIC ACIDS [J].
DAVIS, FA ;
ZHOU, P .
TETRAHEDRON LETTERS, 1994, 35 (41) :7525-7528
[6]   ASYMMETRIC-SYNTHESIS OF 2H-AZIRINES - FIRST ENANTIOSELECTIVE SYNTHESIS OF THE CYTOTOXIC ANTIBIOTIC (R)-(-)-DYSIDAZIRINE [J].
DAVIS, FA ;
REDDY, GV ;
LIU, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (12) :3651-3652
[7]   ASYMMETRIC-SYNTHESIS AND REACTIONS OF CIS-N-(P-TOLUENESULFINYL)AZIRIDINE-2-CARBOXYLIC ACIDS [J].
DAVIS, FA ;
ZHOU, P ;
REDDY, GV .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3243-3245
[8]   DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF L-THREO-SPHINGOSINE AND D-ERYTHRO-SPHINGOSINE [J].
ENDERS, D ;
WHITEHOUSE, DL ;
RUNSINK, J .
CHEMISTRY-A EUROPEAN JOURNAL, 1995, 1 (06) :382-388
[9]   MODEL REACTION FOR BIOSYNTHESIS OF CRININ ALKALOIDS [J].
FRANCK, B ;
LUBS, HJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1968, 7 (03) :223-&
[10]   INHIBITION OF ENTRY OF HIV-1 IN NEURAL CELL-LINES BY ANTIBODIES AGAINST GALACTOSYL CERAMIDE [J].
HAROUSE, JM ;
BHAT, S ;
SPITALNIK, SL ;
LAUGHLIN, M ;
STEFANO, K ;
SILBERBERG, DH ;
GONZALEZSCARANO, F .
SCIENCE, 1991, 253 (5017) :320-323