The use of butane diacetals of glycolic acid as precursors for the synthesis of the phytotoxic calmodulin inhibitor herbarumin II

被引:29
作者
Díez, E [1 ]
Dixon, DJ [1 ]
Ley, SV [1 ]
Polara, A [1 ]
Rodríguez, F [1 ]
机构
[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
关键词
D O I
10.1002/hlca.200390314
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The total synthesis of phytotoxic nonenolide herbarumin 11 (1) has been achieved by implementation of butane diacetal (BDA)-desymmetrised glycolate building blocks. Three of the four stereogenic centres present in the key coupling fragments were generated from both enantiomeric forms of the BDA building block in highly diastereoselective alkylation and aldol reactions.
引用
收藏
页码:3717 / 3729
页数:13
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共 52 条
  • [1] SECONDARY MOLD METABOLITES .41. STRUCTURE AND BIOSYNTHESIS OF CERCOSPORA-BETICOLA TOXIN (CBT)
    ARNONE, A
    NASINI, G
    MERLINI, L
    RAGG, E
    ASSANTE, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (01): : 145 - 151
  • [2] New building blocks for efficient and highly diastereoselective polyol production -: Synthesis and utility of (R′,R′,S,S) and (S′,S′,R,R)-2,3-butane diacetal protected butane tetrol derivatives
    Barlow, JS
    Dixon, DJ
    Foster, AC
    Ley, SV
    Reynolds, DJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (12): : 1627 - 1629
  • [3] Bourgeois D, 2000, ANGEW CHEM INT EDIT, V39, P725, DOI 10.1002/(SICI)1521-3773(20000218)39:4<725::AID-ANIE725>3.0.CO
  • [4] 2-I
  • [5] Bourgeois D, 2000, SYNTHESIS-STUTTGART, P869
  • [6] A simple method to polyhydroxylated olefinic molecules using ring-closing olefin metathesis
    Chang, SB
    Grubbs, RH
    [J]. TETRAHEDRON LETTERS, 1997, 38 (27) : 4757 - 4760
  • [7] Díez E, 2001, ANGEW CHEM INT EDIT, V40, P2906, DOI 10.1002/1521-3773(20010803)40:15<2906::AID-ANIE2906>3.0.CO
  • [8] 2-5
  • [9] A 2,3-butanedione protected chiral glycine equivalent -: a new building block for the stereoselective synthesis of enantiopure N-protected α-amino acids
    Dixon, DJ
    Harding, CI
    Ley, SV
    Tilbrook, DMG
    [J]. CHEMICAL COMMUNICATIONS, 2003, (04) : 468 - 469
  • [10] Dixon DJ, 2001, ANGEW CHEM INT EDIT, V40, P4763, DOI 10.1002/1521-3773(20011217)40:24<4763::AID-ANIE4763>3.0.CO