Pharmaceutical Chemistry (Yoshida Lab.)


  • Prof. Dr. Masahiro Yoshida

  • Dr. Tsukasa Hirokane

Research project

Our research is focused on the chemical synthesis of biologically active molecules and the development of new chemical reactions. We have already achieved for the synthesis of various structurally complex natural products utilizing our novel synthetic methods. In the course of our study about the development of new reactions, we established several novel reactions using transition metal catalyst, which enables to lead the eco-friendly new chemical process.

  1. Transition metal-catalyzed organic reactions
  2. Novel methodology for the synthesis of complex heterocyclic molecules
  3. Efficient synthesis of biologically active molecules


Original articles

  1. A facile synthesis of trisubstituted allenamides by DBU-promoted isomerization of propargylamides.
    T. Hirokane, S. Watanabe, K. Matsumoto, M. Yoshida, Tetrahedron Letters, 61, 152146 (2020).
  2. Catalytic and Aerobic Oxidative Biaryl Coupling of Anilines using a Recyclable Heterogeneous Catalyst for Synthesis of Benzidines and Bicarbazoles.
    K. Matsumoto, Y. Toubaru, S. Tachikawa, A. Miki, K. Sakai, S. Koroki, T. Hirokane, M. Shindo, M. Yoshida, The Journal of Organic Chemistry, 15154-15166 (2020).
  3. Synthesis of Pyrone-annulated 2-Oxabicyclo[3.3.1]nonanes by Palladium-Catalyzed Cyclization of 4-Hydroxy-2-pyrones with Allylic Bisacetates.
    M. Yoshida, M. Shibata, S. Mukae, K. Kinoshita, K. Matsumoto, T. Hirokane, Tetrahedron Letters, 60, 151262 (2019).
  4. A Highly Selective Palladium-Catalyzed Aerobic Oxidative Aniline−Aniline Cross-coupling Reaction.
    K. Matsumoto, S. Takeda, T. Hirokane, M. Yoshida, Organic Letters, 21, 7279-7283 (2019).
  5. Synthesis of Bridgehead-Functionalized Triptycene Quinones via Lewis Acid-Promoted Diels-Alder Reactions of 9-Acyloxyanthracenes.
    K. Matsumoto, R. Nakano, T. Hirokane, M. Yoshida, Tetrahedron Letters, 60, 975-978 (2019).
  6. Synthesis of functionalized 2,3-dihydropyrroles by oxidative radical cyclization of N-sulfonyl β-enamino esters with alkenes.
    M. Yoshida, A. Kobayashi, A. Nakayama, K. Namba, Tetrahedron, 72, 2544-2551 (2016).
  7. Rhodium-Catalyzed Aerobic Oxidative Dehydrogenative Cross-Coupling: Nonsymmetrical Biaryl Amines.
    K. Matsumoto, M. Yoshida, M. Shindo, Angewandte Chemie, International Edition, 55, 5272-5276 (2016).
  8. Direct Cyclization of 1,3-Diaryl Propargylic Alcohols with β-Dicarbonyl Compounds by Palladium-Boric Acid Dual-Catalyst System
    Yoshida, M.; Ohno, S.; Eguchi, S.; Mizuguchi, T.; Matsumoto, K.; Namba, K., Tetrahedron, 72, 5633-5639 (2016).
  9. One-pot synthesis of tri- and tetrasubstituted pyridines by sequential ring-opening/cyclization/oxidation of N-arylmethyl 3-aziridinylpropiolate esters.
    M. Yoshida, T. Mizuguchi, K. Namba, Angewandte Chemie International Edition, 53, 14550-14554 (2014).
  10. Synthesis of substituted tetrahydrocyclobuta[b]benzofurans by palladium-catalyzed substitution/[2+2] cycloaddition of propargylic carbonates with 2-vinylphenols.
    M. Yoshida, S. Ohno, K. Namba, Angewandte Chemie International Edition, 52, 13597-13600 (2013).

Review articles / Books

  1. Yoshida,
    Synthesis of functionalized cyclic molecules by palladium-catalyzed cyclization of propargylic esters with bis-nucleophiles.
    Heterocycles, 87, 1835–1864 (2013).
  2. Yoshida,
    Development of palladium-catalyzed transformations using propargylic compounds.
    Chem. Pharm. Bull., 60, 285–299 (2012).