A chemoenzymatic, enantioconvergent, asymmetric total synthesis of (R)-Fridamycin E

被引:24
作者
Ueberbacher, BJ [1 ]
Osprian, I [1 ]
Mayer, SF [1 ]
Faber, K [1 ]
机构
[1] Graz Univ, Dept Chem Organ & Bioorgan Chem, A-8010 Graz, Austria
关键词
asymmetric synthesis; biotransformations; enzyme catalysis; natural products; total synthesis;
D O I
10.1002/ejoc.200400720
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A chemoenzymatic, asymmetric total synthesis of the antibiotic (R)-fridamycin E has been accomplished following a biocatalytic deracemization procotol. The key step comprises the construction of the chiral side-chain from a functionalized rac-2,2-disubstituted oxirane via a kinetic resolution/stereo-inversion sequence without formation of the undesiredstereoisomer.
引用
收藏
页码:1266 / 1270
页数:5
相关论文
共 18 条
  • [1] EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .26. THE PREPARATION OF CHIRAL INTERMEDIATES FOR ANTHRACYCLINONE SYNTHESIS
    BEAUREGARD, DA
    CAMBIE, RC
    DANSTED, PC
    RUTLEDGE, PS
    WOODGATE, PD
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1995, 48 (03) : 669 - 676
  • [2] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS
    CHEN, CS
    FUJIMOTO, Y
    GIRDAUKAS, G
    SIH, CJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) : 7294 - 7299
  • [3] TOTAL SYNTHESIS OF VINEOMYCINONE-B2 METHYL-ESTER
    DANISHEFSKY, SJ
    UANG, BJ
    QUALLICH, G
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (05) : 1285 - 1293
  • [4] SYNTHESIS OF RAC-FRIDAMYCIN-E AND ENT-FRIDAMYCIN-E
    KROHN, K
    BALTUS, W
    [J]. TETRAHEDRON, 1988, 44 (01) : 49 - 54
  • [5] TOTAL SYNTHESIS OF ANTHRACYCLINONE
    KROHN, K
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (09): : 790 - 807
  • [6] Kroutil W, 1997, SYNTHESIS-STUTTGART, P156
  • [7] EFFICIENT METHOD FOR INTRODUCING VINEOMYCIN-FRIDAMYCIN-TYPE SIDE-CHAIN - TOTAL SYNTHESIS OF FRIDAMYCIN-E
    MATSUMOTO, T
    JONA, H
    KATSUKI, M
    SUZUKI, K
    [J]. TETRAHEDRON LETTERS, 1991, 32 (38) : 5103 - 5106
  • [8] Regioselectivity of Rhodococcus NCIMB 11216 epoxide hydrolase: Applicability of E-values for description of enantioselectivity depends on substrate structure
    Mischitz, M
    Mirtl, C
    Saf, R
    Faber, K
    [J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (07) : 2041 - 2046
  • [9] ASYMMETRIC MICROBIAL HYDROLYSIS OF EPOXIDES
    MISCHITZ, M
    KROUTIL, W
    WANDEL, U
    FABER, K
    [J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (06) : 1261 - 1272
  • [10] Structure and mechanism of the epoxide hydrolase from Agrobacterium radiobacter AD1
    Nardini, M
    Rick, RB
    Janssen, DB
    Dijkstra, BW
    [J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2001, 11 (4-6) : 1035 - 1042