DIPOLAR CYCLOADDITION OF RHODIUM CARBENOIDS WITH VINYL ESTERS - TOTAL SYNTHESIS OF PONGAMOL AND LANCEOLATIN-B

被引:64
|
作者
PIRRUNG, MC
LEE, YR
机构
[1] Department of Chemistry, Duke University P.M. Gross Chemical Laboratory Durham
关键词
RHODIUM ACETATE; EVODONE; KARANJIC ACID;
D O I
10.1016/S0040-4039(00)73399-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method for dipolar cycloaddition of diazocyclohexane-1,3-diones, leading to benzofuran derivatives, has been applied to the total synthesis of natural products from Tephrosia and Pongamia.
引用
收藏
页码:6231 / 6234
页数:4
相关论文
共 50 条
  • [31] 1,2,3-TRIAZOLINES SYNTHESIS BY 1,3-DIPOLAR CYCLOADDITION OF DIAZOALKANES TO OXIME ESTERS
    PERROCHEAU, J
    CARRIE, R
    BULLETIN DES SOCIETES CHIMIQUES BELGES, 1993, 102 (11-12): : 749 - 760
  • [32] Asymmetric formal total synthesis of the stemofoline alkaloids: the evolution, development, and application of a catalytic dipolar cycloaddition cascade
    Shanahan, Charles S.
    Fang, Chao
    Paull, Daniel H.
    Martin, Stephen F.
    TETRAHEDRON, 2013, 69 (36) : 7592 - 7607
  • [33] Total synthesis of (-)-rhazinilam using 1,3-dipolar cycloaddition of optically active miinchnone intermediate
    Sugimoto, Kenji
    Miyakawa, Yuta
    Tokuyama, Hidetoshi
    TETRAHEDRON, 2015, 71 (22) : 3619 - 3624
  • [34] Towards the total synthesis of manzamine a using 1,3 dipolar cycloaddition of azomethine ylides.
    Pih, SM
    Coldham, I
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U370 - U370
  • [35] [1+4]-CYCLOADDITION OF VINYL ISOCYANATES WITH ALKYL ISOCYANIDES - FORMAL TOTAL SYNTHESIS OF ERYSOTRINE
    RIGBY, JH
    QABAR, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) : 8975 - 8976
  • [36] Synthesis of novel multi-functionalized pyrrolidines by [3+2] dipolar cycloaddition of azomethine ylides and vinyl ketones
    Pesic, Marko S.
    Bugarinovic, Jovana P.
    Minic, Aleksandra
    Komatina, Danijela Ilic
    Pejovic, Anka
    Smit, Biljana
    Stevanovic, Dragana
    Damljanovic, Ivan
    MONATSHEFTE FUR CHEMIE, 2019, 150 (04): : 663 - 679
  • [37] SYNTHESIS OF MACROCYCLIC LACTONES APPLYING INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION - SYNTHESIS OF (+/-)-A26771B
    ASAOKA, M
    ABE, M
    MUKUTA, T
    TAKEI, H
    CHEMISTRY LETTERS, 1982, (02) : 215 - 218
  • [38] A convergent synthesis of heterocyclic dendrimers using the 1,3-dipolar cycloaddition reaction of organic azides and acetylenedicarboxylate esters
    Van Wuytswinkel, G
    Verheyde, B
    Compernolle, F
    Toppet, S
    Dehaen, W
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (09): : 1337 - 1340
  • [39] Synthesis of α-trifluoromethyl-β-lactams and esters of β-amino acids via 1,3-dipolar cycloaddition of nitrones to fluoroalkenes
    Jakowiecki, Jakub
    Loska, Rafal
    Makosza, Mieczyslaw
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14): : 5436 - 5441
  • [40] Mild and efficient method for the synthesis of flavones by InCl3-mediated cyclization of 1,3-diketones:: Concise total synthesis of lanceolatin B
    Lee, Yong Rok
    Kang, Keon Yong
    LETTERS IN ORGANIC CHEMISTRY, 2007, 4 (06) : 440 - 444