Solid-phase total synthesis of the pentacyclic system lamellarins U and L

被引:80
作者
Cironi, P
Manzanares, I
Albericio, F
Alvarez, M
机构
[1] Univ Barcelona, Inst Biomed Res, Dept Organ Chem, E-08028 Barcelona, Spain
[2] Univ Barcelona, Fac Pharm, Organ Chem Lab, Barcelona, Spain
[3] Pharma Mar, Colmenar Viejo 28770, Spain
关键词
D O I
10.1021/ol0351192
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A total solid-phase synthesis of lamellarins U and L has been achieved. The conversion of an aldehyde group into a formate by a Baeyer-Villiger reaction and a intramolecular [3 + 2] cycloaddition of a 3,4-dihydroisoquinolinium salt over a triple bond comprise the key steps of the process. Each transformation has been controlled with the proper spectroscopic and analytical methods.
引用
收藏
页码:2959 / 2962
页数:4
相关论文
共 42 条
  • [1] Albericio F, 2000, SOLID-PHASE SYNTHESIS, P275
  • [2] METABOLITIES OF THE MARINE PROSOBRANCH MOLLUSK LAMELLARIA SP
    ANDERSEN, RJ
    FAULKNER, DJ
    HE, CH
    VANDUYNE, GD
    CLARDY, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (19) : 5492 - 5495
  • [3] Perspective articles on the utility and application of solution-phase combinatorial chemistry
    Baldino, CM
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2000, 2 (02): : 89 - 103
  • [4] Convergent total synthesis of lamellarin K
    Banwell, M
    Flynn, B
    Hockless, D
    [J]. CHEMICAL COMMUNICATIONS, 1997, (23) : 2259 - 2260
  • [5] Selective cleavage of isopropyl aryl ethers by aluminum trichloride
    Banwell, MG
    Flynn, BL
    Stewart, SG
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (24) : 9139 - 9144
  • [6] Berteina S, 1998, SYNLETT, P676
  • [7] Total synthesis of ningalin B utilizing a heterocyclic azadiene Diels-Alder reaction and discovery of a new class of potent multidrug resistant (MDR) reversal agents
    Boger, DL
    Soenen, DR
    Boyce, CW
    Hedrick, MP
    Jin, Q
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (08) : 2479 - 2483
  • [8] Breinbauer R, 2002, ANGEW CHEM INT EDIT, V41, P2879
  • [9] Proteomics in drug discovery
    Burbaum, J
    Tobal, GM
    [J]. CURRENT OPINION IN CHEMICAL BIOLOGY, 2002, 6 (04) : 427 - 433
  • [10] New lamellarin alkaloids from the Australian ascidian, Didemnum chartaceum
    Davis, RA
    Carroll, AR
    Pierens, GK
    Quinn, RJ
    [J]. JOURNAL OF NATURAL PRODUCTS, 1999, 62 (03): : 419 - 424