Application of arene-ruthenium chemistry to a formal total synthesis of OF 4949 III

被引:50
|
作者
Pearson, AJ
Zhang, PL
Lee, K
机构
[1] Department of Chemistry, Case Western Reserve University, Cleveland
来源
JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 19期
关键词
D O I
10.1021/jo960956l
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convergent formal total synthesis of OF 4949 III is described. Arene-ruthenium chemistry was used in the construction of the diaryl ether linkage in high yield, and cycloamidation under high dilution conditions (0.005 M) was achieved using DPPA as coupling reagent. SmI2 was used to reductively remove the 2-iodoethyl ester protecting group in the presence of DMPU or HMPA.
引用
收藏
页码:6581 / 6586
页数:6
相关论文
共 50 条
  • [1] A FORMAL TOTAL SYNTHESIS OF THE ACE-INHIBITOR K-13 - AN APPLICATION OF ARENE-RUTHENIUM CHEMISTRY TO COMPLEX CHEMICAL SYNTHESIS
    PEARSON, AJ
    LEE, KS
    JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09): : 2304 - 2313
  • [2] THE SYNTHESIS AND CHARACTERIZATION OF SOME ARENE-RUTHENIUM CLUSTER COMPOUNDS
    JOHNSON, BFG
    DYSON, PJ
    BRAGA, D
    GREPIONI, F
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 203 : 15 - INOR
  • [3] Synthesis and fluorescent properties of arene-ruthenium(II) complexes
    Budzisz, Elzbieta
    Pastuszko, Adam
    Kupcewicz, Bogumila
    JOURNAL OF BIOLOGICAL INORGANIC CHEMISTRY, 2014, 19 : S787 - S788
  • [4] Preparation of donor-σ-acceptor molecules using arene-ruthenium chemistry
    Pearson, AJ
    Hwang, JJ
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (11): : 3466 - 3472
  • [5] Synthesis and characterization of water-soluble arene-ruthenium complexes and their application in biphasic olefin oxidation
    Gichumbi, Joel M.
    Friedrich, Holger B.
    Omondi, Bernard
    JOURNAL OF COORDINATION CHEMISTRY, 2019, 72 (01) : 135 - 147
  • [6] Synthesis and structural chemistry of arene-ruthenium half-sandwich complexes bearing an oxazolinyl-carbene ligand
    Poyatos, Macarena
    Maisse-Francois, Aline
    Bellemin-Laponnaz, Stephane
    Peris, Eduardo
    Gade, Lutz H.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (12) : 2713 - 2720
  • [7] Synthesis, structure and redox behaviour of tethered arene-ruthenium(II) complexes
    Bennett, MA
    Edwards, AJ
    Harper, JR
    Khimyak, T
    Willis, AC
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 629 (1-2) : 7 - 18
  • [8] Arene-Ruthenium Chemistry and Bronsted Acid Catalysis of a Chiral Phosphane-Hydroxyl Ligand
    Carmona, Daniel
    Pilar Lamata, M.
    Pardo, Pilar
    Rodriguez, Ricardo
    Lahoz, Fernando J.
    Garcia-Orduna, Pilar
    Alkorta, Ibon
    Elguero, Jose
    Oro, Luis A.
    ORGANOMETALLICS, 2014, 33 (03) : 616 - 619
  • [9] A convergent approach towards the synthesis of ristocetin analogs using arene-ruthenium complexes
    Pearson, AJ
    Chelliah, MV
    Bignan, G
    Zhang, PL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 212 : 169 - ORGN
  • [10] Total synthesis of the cyclic biphenyl ether peptides K-13 and OF4949-III via SNAr macrocyclization of peptidyl ruthenium pi-arene complexes
    Janetka, JW
    Rich, DH
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (28) : 6488 - 6495