A short synthetic pathway to a fully-functionalized southern hemisphere of the antitumor macrolide bryostatin 1

被引:21
作者
Hale, KJ [1 ]
Frigerio, M [1 ]
Manaviazar, S [1 ]
机构
[1] UCL, Dept Chem, Christopher Ingold Labs, London WC1H 0AJ, England
关键词
D O I
10.1021/ol016800b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] An 18-step asymmetric synthesis of the bryostatin 1 "southern hemisphere" fragment (1) has been developed. Key steps include an aldol reaction between 6 and 7 and a dehydration to establish the (E)-exocyclic alkene in 2 and a stereoselective Luche reduction and protection with TESOTf to access 1.
引用
收藏
页码:3791 / 3794
页数:4
相关论文
共 47 条
  • [1] An approach to the synthesis of the C(17)-C(27) fragment of bryostatins
    Baxter, J
    Mata, EG
    Thomas, EJ
    [J]. TETRAHEDRON, 1998, 54 (47) : 14359 - 14376
  • [2] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS
    BLANCHETTE, MA
    CHOY, W
    DAVIS, JT
    ESSENFELD, AP
    MASAMUNE, S
    ROUSH, WR
    SAKAI, T
    [J]. TETRAHEDRON LETTERS, 1984, 25 (21) : 2183 - 2186
  • [3] BRYOSTATINS - THE ASYMMETRIC-SYNTHESIS OF C1-C9 AND C11-C16 FRAGMENTS
    DEBRABANDER, J
    VANHESSCHE, K
    VANDEWALLE, M
    [J]. TETRAHEDRON LETTERS, 1991, 32 (24) : 2821 - 2824
  • [4] DEBRABANDER J, 1994, SYNLETT, P231
  • [5] DEBRABANDER J, 1994, SYNTHESIS-STUTTGART, P855
  • [6] Bryostatin: A novel asymmetric synthesis of the C-27-C-34 fragment starting from (R)-carvone as chiral template
    DeBrabander, J
    Kulkarni, BA
    GarciaLopez, R
    Vandewalle, M
    [J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (11) : 1721 - 1724
  • [7] SYNTHESIS OF 1,3-DIOL SYNTHONS FROM EPOXY AROMATIC PRECURSORS - AN APPROACH TO THE CONSTRUCTION OF POLYACETATE-DERIVED NATURAL-PRODUCTS
    EVANS, DA
    GAUCHETPRUNET, JA
    CARREIRA, EM
    CHARETTE, AB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) : 741 - 750
  • [8] Total synthesis of bryostatin 2
    Evans, DA
    Carter, PH
    Carreira, EM
    Charette, AB
    Prunet, JA
    Lautens, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (33) : 7540 - 7552
  • [9] CONTROL OF REMOTE ENOATE GEOMETRY IN THE BRYOSTATINS WITH A TETHERED HORNER-WADSWORTH-EMMONS REAGENT
    EVANS, DA
    CARREIRA, EM
    [J]. TETRAHEDRON LETTERS, 1990, 31 (33) : 4703 - 4706
  • [10] An approach to the C(17)-C(24) fragment of bryostatins: applications of stereoselective trisubstituted alkene formation by palladium(0) catalysed coupling of enol acetates and vinylic bromides
    Gracia, J
    Thomas, EJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (17): : 2865 - 2871