The application of vinylogous iminium salt derivatives to a regiocontrolled and efficient relay synthesis of Lukianol A and related marine natural products

被引：38
|
作者：
Gupton, JT [1 ]
Krumpe, KE
Burnham, BS
Webb, TM
Shuford, JS
Sikorski, JA
机构：
[1] Univ Richmond, Dept Chem, Richmond, VA 23173 USA
[2] Univ N Carolina, Dept Chem, Asheville, NC 28804 USA
[3] GD Searle & Co, Res & Dev, St Louis, MO 63198 USA
来源：
TETRAHEDRON | 1999年 / 55卷 / 51期
关键词：
pyrroles; iminium salts; enals; natural products;
D O I：
10.1016/S0040-4020(99)00926-6
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Numerous novel pyrrole containing marine natural products have been shown to possess interesting biological properties. These compounds have been the synthetic targets of several research groups and we have previously reported synthetic methods which utilize vinylogous iminium salt derivatives as building blocks for analogous pyrrole systems. We now report a novel and regiocontrolled synthesis of a known pyrrole synthetic precursor to the compounds Lukianol A and Lammelarin O dimethyl ether based on this synthetic methodology. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：14515 / 14522
页数：8
相关论文
共 50 条
  • [1] The application of vinylogous iminium salt derivatives to an efficient relay synthesis of the pyrrole containing alkaloids polycitone A and B
    Gupton, JT
    Miller, RB
    Krumpe, KE
    Clough, SC
    Banner, EJ
    Kanters, RPF
    Du, KX
    Keertikar, KM
    Lauerman, NE
    Solano, JM
    Adams, BR
    Callahan, DW
    Little, BA
    Scharf, AB
    Sikorski, JA
    TETRAHEDRON, 2005, 61 (07) : 1845 - 1854
  • [2] The application of vinylogous iminium salt derivatives to the regiocontrolled preparation of heterocyclic appended pyrazoles
    Gupton, JT
    Clough, SC
    Miller, RB
    Norwood, BK
    Hickenboth, CR
    Chertudi, IB
    Cutro, SR
    Petrich, SA
    Hicks, FA
    Wilkinson, DR
    Sikorski, JA
    TETRAHEDRON, 2002, 58 (27) : 5467 - 5474
  • [3] The application of vinylogous iminium salt derivatives and microwave accelerated Vilsmeier-Haack reactions to efficient relay syntheses of the polycitone and storniamide natural products
    Gupton, John T.
    Banner, Edith J.
    Sartin, Melissa D.
    Coppock, Matthew B.
    Hempel, Jonathan E.
    Kharlamova, Anastasia
    Fisher, Daniel C.
    Giglio, Ben C.
    Smith, Kristin L.
    Keough, Matt J.
    Smith, Timothy M.
    Kanters, Rene P. F.
    Dominey, Raymond N.
    Sikorski, James A.
    TETRAHEDRON, 2008, 64 (22) : 5246 - 5253
  • [4] The application of vinylogous iminium salt derivatives to an efficient synthesis of the pyrrole containing alkaloids Rigidin and Rigidin E
    Gupton, John T.
    Banner, Edith J.
    Scharf, Austin B.
    Norwood, Bradley K.
    Kanters, Rene P. F.
    Dominey, Raymond N.
    Hempel, Jonathan E.
    Kharlamova, Anastasia
    Bluhn-Chertudi, Itta
    Hickenboth, Charles R.
    Little, Barrett A.
    Sartin, Melissa D.
    Coppock, Matthew B.
    Krumpe, Keith E.
    Burnham, Bruce S.
    Holt, Herman
    Du, Karen X.
    Keertikar, Kartik M.
    Diebes, Anthony
    Ghassemi, Shahnaz
    Sikorski, James A.
    TETRAHEDRON, 2006, 62 (35) : 8243 - 8255
  • [5] The application of vinylogous iminium salt derivatives to the synthesis of Ningalin B hexamethyl ether
    Gupton, JT
    Clough, SC
    Miller, RB
    Lukens, JR
    Henry, CA
    Kanters, RPF
    Sikorski, JA
    TETRAHEDRON, 2003, 59 (02) : 207 - 215
  • [6] 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
  • [7] The application of disubstituted vinylogous iminium salts and related synthons to the regiocontrolled preparation of unsymmetrical 2,3,4-trisubstituted pyrroles
    Gupton, JT
    Krumpe, KE
    Burnham, BS
    Dwornik, KA
    Petrich, SA
    Du, KX
    Bruce, MA
    Vu, P
    Vargas, M
    Keertikar, KM
    Hosein, KN
    Jones, CR
    Sikorski, JA
    TETRAHEDRON, 1998, 54 (20) : 5075 - 5088
  • [8] The application of vinylogous iminium salts and related synthons to the regiocontrolled preparation of 2,3- and 2,5-disubstituted pyrroles
    Gupton, JT
    Petrich, SA
    Smith, LL
    Bruce, MA
    Vu, P
    Du, KX
    Dueno, EE
    Jones, CR
    Sikorski, JA
    TETRAHEDRON, 1996, 52 (20) : 6879 - 6892
  • [9] NEW APPROACHES ON SYNTHESIS OF ISOQUINOLINE DERIVATIVES RELATED WITH NATURAL PRODUCTS
    BROSSI, A
    TRANSACTIONS OF THE NEW YORK ACADEMY OF SCIENCES, 1966, 28 (06): : 685 - &
  • [10] Electrochemical synthesis of spiroisoxazole derivatives and its application to natural products
    Ogamino, T
    Ishikawa, Y
    Nishiyama, S
    HETEROCYCLES, 2003, 61 : 73 - +
12345