Biomimetic syntheses of lamellarin and lukianol-type alkaloids

被引:43
|
作者
Peschko, Christian [1 ]
Winklhofer, Christian [1 ]
Terpin, Andreas [1 ]
Steglich, Wolfgang [1 ]
机构
[1] Univ Munich, Dept Chem, D-81377 Munich, Germany
来源
SYNTHESIS-STUTTGART | 2006年 / 18期
关键词
biomimetic synthesis; marine alkaloids; pyrroles; lamellarins; lukianol A;
D O I
10.1055/s-2006-950191
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The formation of 3,4-diarylpyrrole-2,5-dicarboxylic acids from arylpyruvic acids and 2-arylethylamines was used as a key step for the synthesis of several marine pyrrole alkaloids. The utility of this method is illustrated through the development of syntheses of ningalin B (5), lamellarins G (11a) and K (11b), lukianol A (32), and a lukianol-lamellarin hybrid (24).
引用
收藏
页码:3048 / 3057
页数:10
相关论文
共 50 条
  • [1] Synthesis of lamellarin R, lukianol A, lamellarin O and their analogues
    Satyanarayana, Iddum
    Yang, Ding-Yah
    Liou, Teau-Jiuan
    RSC ADVANCES, 2020, 10 (70) : 43168 - 43174
  • [2] Biomimetic Syntheses of the Flindersial Alkaloids
    Vallakati, Ravikrishna
    May, Jeremy A.
    SYNLETT, 2012, (18) : 2577 - 2581
  • [4] Convergent syntheses of the pyrrolic marine natural products lamellarin-O, lamellarin-Q, lukianol-A and some more highly oxygenated congeners
    Banwell, MG
    Flynn, BL
    Hamel, E
    Hockless, DCR
    CHEMICAL COMMUNICATIONS, 1997, (02) : 207 - 208
  • [5] Total syntheses of lamellarin D and H. The first synthesis of lamellarin-class marine alkaloids
    Ishibashi, F
    Miyazaki, Y
    Iwao, M
    TETRAHEDRON, 1997, 53 (17) : 5951 - 5962
  • [6] Total syntheses of ningalin A, lamellarin O, lukianol A, and permethyl storniamide A utilizing heterocyclic azadiene Diels-Alder reactions
    Boger, DL
    Boyce, CW
    Labroli, MA
    Sehon, CA
    Jin, Q
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (01) : 54 - 62
  • [7] Biomimetic syntheses of alkaloids based on tetrahydropyridine
    Wanner, MJ
    Koomen, GJ
    PURE AND APPLIED CHEMISTRY, 1996, 68 (11) : 2051 - 2056
  • [8] Biomimetic Total Syntheses of Clavine Alkaloids
    Chaudhuri, Saikat
    Bhunia, Subhajit
    Roy, Avishek
    Das, Mrinal K.
    Bisai, Alakesh
    ORGANIC LETTERS, 2018, 20 (01) : 288 - 291
  • [9] Biomimetic total syntheses of prenylated indole alkaloids
    Williams, Robert M.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [10] FACILE BIOMIMETIC SYNTHESES OF DIBENZAZONINE AND APORPHINE ALKALOIDS
    KUPCHAN, SM
    KIM, C
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (19) : 5623 - 5625