A synthesis of the welwistatin core

被引:85
作者
Lauchli, Ryan [1 ]
Shea, Kenneth J. [1 ]
机构
[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
关键词
D O I
10.1021/ol0620747
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] An approach to the core structure of the microtubule-targeting agent welwistatin is described. The approach utilizes the type 2 intramolecular Diels-Alder reaction, with indole serving as the tether between diene and dienophile, to form the natural product's characteristic bicyclo[4.3.1] decane skeleton.
引用
收藏
页码:5287 / 5289
页数:3
相关论文
共 27 条
  • [1] Synthetic studies on N-methylwelwitindolinone C isothiocyanate (welwistatin) and related substructures
    Avendaño, C
    Menéndez, JC
    [J]. CURRENT ORGANIC SYNTHESIS, 2004, 1 (01) : 65 - 82
  • [2] Enantioselective total syntheses of welwitindolinone A and fischerindoles I and G
    Baran, PS
    Richter, JM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (44) : 15394 - 15396
  • [3] Rapid access to the welwitindolinone alkaloid skeleton by cyclization of indolecarboxaldehyde substituted cyclohexanones
    Baudoux, J
    Blake, AJ
    Simpkins, NS
    [J]. ORGANIC LETTERS, 2005, 7 (19) : 4087 - 4089
  • [4] Bear BR, 2001, ANGEW CHEM INT EDIT, V40, P821
  • [5] A synthetic entry to 2,3-fused ring indole derivatives by ring-closing metathesis reactions
    Bennasar, ML
    Zulaica, E
    Tummers, S
    [J]. TETRAHEDRON LETTERS, 2004, 45 (33) : 6283 - 6285
  • [6] Aryllead(IV) reagents in synthesis:: Formation of the C11 quaternary center of N-methylwelwitindolinone C isothiocyanate
    Deng, HB
    Konopelski, JP
    [J]. ORGANIC LETTERS, 2001, 3 (19) : 3001 - 3004
  • [7] Enyne metathesis (enyne bond reorganization)
    Diver, ST
    Giessert, AJ
    [J]. CHEMICAL REVIEWS, 2004, 104 (03) : 1317 - 1382
  • [8] An approach to the total synthesis of welwistatin
    Greshock, Thomas J.
    Funk, Raymond L.
    [J]. ORGANIC LETTERS, 2006, 8 (12) : 2643 - 2645
  • [9] Oxidized welwitindolinones from terrestrial Fischerella spp.
    Jimenez, JI
    Huber, U
    Moore, RE
    Patterson, GML
    [J]. JOURNAL OF NATURAL PRODUCTS, 1999, 62 (04): : 569 - 572
  • [10] Microtubules as a target for anticancer drugs
    Jordan, MA
    Wilson, L
    [J]. NATURE REVIEWS CANCER, 2004, 4 (04) : 253 - 265