STEREOCONTROLLED SYNTHETIC ENTRIES TO HOMOCHIRAL HYDROXYLATED NORBORNENE DERIVATIVES - FORMAL SYNTHESIS OF SOME CARBOCYCLIC NUCLEOSIDES

被引:23
作者
DIAZ, M [1 ]
IBARZO, J [1 ]
JIMENEZ, JM [1 ]
ORTUNO, RM [1 ]
机构
[1] UNIV AUTONOMA BARCELONA,DEPT QUIM,E-08193 BARCELONA,SPAIN
关键词
D O I
10.1016/S0957-4166(00)80493-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Several homochiral hydroxylated norbornene derivatives have been synthesized from D-mannitol. Stereocontrolled Diels-Alder cycloadditions and stereospecific hydroxylations are key processes for the creation of the stereogenic centers in the target molecules. These compounds are real or potential precursors in the synthesis of carbocyclic nucleosides and related products.
引用
收藏
页码:129 / 140
页数:12
相关论文
共 15 条
  • [1] SYNTHESIS AND DIELS-ALDER REACTIONS OF HOMOCHIRAL 2-SULFINYLMALEATES WITH CYCLOPENTADIENE
    ALONSO, I
    CID, MB
    CARRETERO, JC
    RUANO, JLG
    HOYOS, MA
    [J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (12) : 1193 - 1207
  • [2] ENANTIOSELECTIVE SYNTHESIS OF THE CARBOCYCLIC NUCLEOSIDES (-)-ARISTEROMYCIN AND (-)-NEPLANOCIN-A BY A CHEMICOENZYMATIC APPROACH
    ARITA, M
    ADACHI, K
    ITO, Y
    SAWAI, H
    OHNO, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (12) : 4049 - 4055
  • [3] OXIDATION OF ALPHA,BETA-UNSATURATED ALDEHYDES
    BAL, BS
    CHILDERS, WE
    PINNICK, HW
    [J]. TETRAHEDRON, 1981, 37 (11) : 2091 - 2096
  • [4] DIELS-ALDER CYCLO-ADDITIONS OF CHIRAL BUTENOLIDES WITH CYCLOPENTADIENE - ENDO EXO SELECTIVITY
    BATLLORI, R
    FONT, J
    MONSALVATJE, M
    ORTUNO, RM
    SANCHEZFERRANDO, F
    [J]. TETRAHEDRON, 1989, 45 (06) : 1833 - 1838
  • [5] SYNTHESIS OF CHIRAL CARBOCYCLIC NUCLEOSIDES
    BORTHWICK, AD
    BIGGADIKE, K
    [J]. TETRAHEDRON, 1992, 48 (04) : 571 - 623
  • [6] A VERSATILE AND HIGHLY STEREOCONTROLLED SYNTHETIC APPROACH TO HOMOCHIRAL POLYFUNCTIONAL NORBORNENE AND NORBORNANE DERIVATIVES
    CASAS, R
    IBARZO, J
    JIMENEZ, JM
    ORTUNO, RM
    [J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (04) : 669 - 680
  • [7] 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
    CASAS, R
    ORTUNO, RM
    [J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (09) : 1205 - 1212
  • [8] CHEN Z, UNPUB
  • [9] SYNTHESIS FROM (-)-ARISTEROMYCIN AND X-RAY STRUCTURE OF (-)-CARBOVIR
    EXALL, AM
    JONES, MF
    MO, CL
    MYERS, PL
    PATERNOSTER, IL
    SINGH, H
    STORER, R
    WEINGARTEN, GG
    WILLIAMSON, C
    BRODIE, AC
    COOK, J
    LAKE, DE
    MEERHOLZ, CA
    TURNBULL, PJ
    HIGHCOCK, RM
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (10): : 2467 - 2477
  • [10] STREPTOMYCES CITRICOLOR NOV SP AND A NEW ANTIBIOTIC ARISTEROMYCIN
    KUSAKA, T
    YAMAMOTO, H
    SHIBATA, M
    MUROI, M
    KISHI, T
    MIZUNO, K
    [J]. JOURNAL OF ANTIBIOTICS, 1968, 21 (04) : 255 - &