Studies towards the total synthesis of palau'amine. Formation of 4,5-dihydropyrrole-2-carboxylate intermediates by alkene-enamide ring-closing metathesis

被引:75
作者
Katz, JD [1 ]
Overman, LE [1 ]
机构
[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
关键词
palau'amime; enamide; ring-closing metathesis; 4,5-dihydro-pyrrole-2-carboxylate; azomethine imine cycloaddition;
D O I
10.1016/j.tet.2004.06.140
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly functionalized 4,5-dihydropyrrole-2-carboxylate is assembled by alkene-enamide ring-closing metathesis. Subsequent intramolecular azomethine imine dipolar cycloaddition provides a triazacyclopenta[cd]pentalene intermediate of potential use in a total synthesis of palau'amine. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9559 / 9568
页数:10
相关论文
共 49 条
  • [1] Synthesis and anticonvulsant activities of (R)-(O)-methylserine derivatives
    Andurkar, SV
    Stables, JP
    Kohn, H
    [J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (21) : 3841 - 3854
  • [2] Selective isomerization of a terminal olefin catalyzed by a ruthenium complex: The synthesis of indoles through ring-closing metathesis
    Arisawa, M
    Terada, Y
    Nakagawa, M
    Nishida, A
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (24) : 4732 - 4734
  • [3] Tandem radical cyclisation of enamides mediated by tin hydride; pyrrolizidinone or indolizidinone ring formation
    Baker, SR
    Burton, KI
    Parsons, AF
    Pons, JF
    Wilson, M
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (04): : 427 - 436
  • [4] Stereocontrolled synthesis of triazacyclopenta[cd]pentalenes by intramolecular 1,3-dipolar cycloaddition reactions of azomethine imines
    Bélanger, G
    Hong, FT
    Overman, LE
    Rogers, BN
    Tellew, JE
    Trenkle, WC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (22) : 7880 - 7883
  • [5] Natural guanidine derivatives
    Berlinck, RGS
    [J]. NATURAL PRODUCT REPORTS, 2002, 19 (05) : 617 - 649
  • [6] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES
    DESS, DB
    MARTIN, JC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) : 4155 - 4156
  • [7] Enantioselective strategy to the spirocyclic core of palau'amine and related bisguanidine marine alkaloids
    Dilley, AS
    Romo, D
    [J]. ORGANIC LETTERS, 2001, 3 (10) : 1535 - 1538
  • [8] NEW ENANTIOSELECTIVE APPROACH TO ALPHA-ALLOKAINOIDS BY MICHAEL ADDITION TO CHIRAL 4-SUBSTITUTED 2,3-DIDEHYDROPROLINATE
    EZQUERRA, J
    ESCRIBANO, A
    RUBIO, A
    REMUINAN, MJ
    VAQUERO, JJ
    [J]. TETRAHEDRON LETTERS, 1995, 36 (34) : 6149 - 6152
  • [9] Marine natural products
    Faulkner, DJ
    [J]. NATURAL PRODUCT REPORTS, 2002, 19 (01) : 1 - 48
  • [10] Fürstner A, 2002, ADV SYNTH CATAL, V344, P567, DOI 10.1002/1615-4169(200208)344:6/7<567::AID-ADSC567>3.0.CO