Siloxane-based cross-coupling of bromopyridine derivatives: Studies for the synthesis of streptonigrin and lavendamycin

被引:39
|
作者
McElroy, WT [1 ]
DeShong, P [1 ]
机构
[1] Univ Maryland, Dept Chem & Biochem, College Pk, MD 20742 USA
关键词
D O I
10.1021/ol0357503
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Highly functionalized 4-bromopyridines were prepared and found to undergo fluoride-promoted, Pd-catalyzed cross-coupling with aryltrialkoxysilanes to give sterically demanding biaryls. The 3-nitro-4-bromopyridine derivative coupled in good yield with TBAT (tetrabutylammonium triphenyidifluorosilicate) to provide a biaryl adduct that serves as a model system for the total synthesis of the antitumor antibiotics streptonigrin and lavendamycin.
引用
收藏
页码:4779 / 4782
页数:4
相关论文
共 50 条
  • [21] One-Pot Cross-Coupling of Diborylmethane for the Synthesis of Dithienylmethane Derivatives
    Endo, Kohei
    Ishioka, Takafumi
    Shibata, Takanori
    SYNLETT, 2014, 25 (15) : 2184 - 2188
  • [22] Synthesis of β2-homophenylalanine derivatives by Negishi cross-coupling reactions
    Bartrum, Hannah E.
    Adams, Harry
    Caggiano, Lorenzo
    Jackson, Richard F. W.
    TETRAHEDRON, 2008, 64 (17) : 3701 - 3712
  • [23] Synthesis of arylated chalcone derivatives via palladium cross-coupling reactions
    da Costa, Rafaela G. M.
    Farias, Francisco R. L.
    Back, Davi
    Limberger, Jones
    TETRAHEDRON LETTERS, 2018, 59 (08) : 771 - 775
  • [24] Synthesis of α-Alkynyl-β,β,β-trifluoroalanine Derivatives by Sonogashira Cross-Coupling Reaction
    Shchetnikov, Grigorii T.
    Zotova, Maria A.
    Bruneau, Christian
    Dixneuf, Pierre H.
    Osipov, Sergey N.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (08) : 1587 - 1592
  • [25] FACILE SYNTHESIS OF THYMIDINE DERIVATIVES BY CROSS-COUPLING OF 5-HALOGENOURIDINE DERIVATIVES WITH TRIMETHYLALUMINUM
    HIROTA, K
    KITADE, Y
    KANBE, Y
    ISOBE, Y
    MAKI, Y
    SYNTHESIS-STUTTGART, 1993, (02): : 213 - 215
  • [26] Improvements in cross coupling reactions of hypervalent siloxane derivatives
    Mowery, ME
    DeShong, P
    ORGANIC LETTERS, 1999, 1 (13) : 2137 - 2140
  • [27] Synthesis of siloxane-based PAMAM dendrimers and luminescent properties of their lanthanide complexes
    Niu, Yuzhong
    Lu, Haifeng
    Wang, Dengxu
    Yue, Yuanzhi
    Feng, Shengyu
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (02) : 544 - 550
  • [28] Versatile synthesis of siloxane-based graft copolymers with tunable grafting density
    D'Ambra, Colton A.
    Czuczola, Michael
    Getty, Patrick T.
    Murphy, Elizabeth A.
    Abdilla, Allison
    Biswas, Souvagya
    Mecca, Jodi M.
    Bekemeier, Thomas D.
    Swier, Steven
    Hawker, Craig J.
    Bates, Christopher M.
    JOURNAL OF POLYMER SCIENCE, 2024, 62 (01) : 92 - 101
  • [29] Efforts directed toward the synthesis of colchicine: Application of palladium-catalyzed siloxane cross-coupling methodology
    Seganish, WM
    Handy, CJ
    DeShong, P
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (22): : 8948 - 8955
  • [30] SYNTHETIC STUDIES VIA THE CROSS-COUPLING REACTION OF ORGANOBORON DERIVATIVES WITH ORGANIC HALIDES
    SUZUKI, A
    PURE AND APPLIED CHEMISTRY, 1991, 63 (03) : 419 - 422