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
  • [21] Approach to Isomers and Structural Relatives of the Lamellarin Alkaloids
    Tauber, Johannes
    Imbri, Dennis
    Colligs, Vanessa C.
    Opatz, Till
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2014, 69 (05): : 627 - 640
  • [22] BIOMIMETIC SYNTHESES OF INDOLE ALKALOIDS .11. SYNTHESES OF BETA-CARBOLINE AND INDOLOAZEPINE INTERMEDIATES
    KUEHNE, ME
    BOHNERT, JC
    BORNMANN, WG
    KIRKEMO, CL
    KUEHNE, SE
    SEATON, PJ
    ZEBOVITZ, TC
    JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (07): : 919 - 924
  • [23] Biomimetic Total Syntheses of Ergot Alkaloids via Decarboxylative Giese Coupling
    Ge, Yuhua
    Wang, Hang
    Wang, Hua-Nan
    Yu, Shu-Sheng
    Yang, Rui
    Chen, Xingyue
    Zhao, Qin
    Chen, Gang
    ORGANIC LETTERS, 2021, 23 (02) : 370 - 375
  • [24] Recent Advances in Lamellarin Alkaloids: Isolation, Synthesis and Activity
    Pla, D.
    Albericio, F.
    Alvarez, M.
    ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY, 2008, 8 (07) : 746 - 760
  • [25] A NEW, TITANIUM-MEDIATED APPROACH TO PYRROLES - FIRST SYNTHESIS OF LUKIANOL-A AND LAMELLARIN-O DIMETHYL ETHER
    FURSTNER, A
    WEINTRITT, H
    HUPPERTS, A
    JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (20): : 6637 - 6641
  • [26] BIOGENETIC TYPE SYNTHESES OF APORPHINE ALKALOIDS, ISOBOLDINE AND GLAUCINE
    KAMETANI, T
    SUGAHARA, T
    YAGI, H
    FUKUMOTO, K
    TETRAHEDRON, 1969, 25 (17) : 3667 - &
  • [27] BIOGENETIC TYPE SYNTHESES OF APORPHINE ALKALOIDS - ISOBOLDINE AND CORYDINE
    JACKSON, AH
    MARTIN, JA
    CHEMICAL COMMUNICATIONS, 1965, (18) : 420 - &
  • [28] A biomimetic approach to the discorhabdin alkaloids: Total syntheses of discorhabdins C and E and dethiadiscorhabdin D
    Aubart, KM
    Heathcock, CH
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01): : 16 - 22
  • [29] The application of vinylogous iminium salt derivatives to efficient formal syntheses of the marine alkaloids lamellarin G trimethyl ether and ningalin B
    Gupton, John T.
    Giglio, Benjamin C.
    Eaton, James E.
    Rieck, Elizabeth A.
    Smith, Kristin L.
    Keough, Matthew J.
    Barelli, Peter J.
    Firich, Lauren T.
    Hempel, Jonathan E.
    Smith, Timothy M.
    Kanters, Rene P. F.
    TETRAHEDRON, 2009, 65 (22) : 4283 - 4292
  • [30] Facilitating Biomimetic Syntheses of Borrerine Derived Alkaloids by Means of Flow-Chemical Methods
    Kamptmann, Sonja B.
    Ley, Steven V.
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2015, 68 (04) : 693 - 696