Administrative Contact: Sarah Quilty
The major research efforts of the Kishi group are focused on the total syntheses of various complex natural products, typified by the completed works of neurotoxins (palytoxin, tetrodotoxin, etc.), antitumor antibiotics (halichondrins, mitomycins, etc.), polyether antibiotics (lasalocid A, monensin, etc.), metabolites of microorganisms (gliotoxins, etc.), and others. In order to carry out these syntheses, not only new synthetic strategies but also new synthetic methods are investigated. Current programs in this area include: the total synthesis of halichondrin A, an antitumor polyether macrolide isolated from marine sponges, and the development of catalytic asymmetric Cr-mediated coupling reactions.
In addition, the Kishi group has extensively been engaged with the structure elucidation of complex natural products via organic synthesis, as exemplified by the stereochemistry assignment of palytoxin and maitotoxin. This line of work has evolved to the universal NMR database approach, which allows assignment of the relative and absolute configuration of unknown compounds without degradation and/or derivatization. Noteworthily, the stereochemistry of mycolactones, the causative toxins of Buruli ulcer, has been established by this approach.
- “Palytoxin: An Inexhaustible Source Of Inspiration Personal Perspective”, Yoshito Kishi, Tetrahedron, 58, 6239 (2002).
- “Research Summary of Kishi Group”, Yoshito Kishi, Heterocycles, 72, 7 (2007).
- “Toolbox Approach to the Search for Effective Ligands for Catalytic Asymmetric Cr-Mediated Coupling Reactions”, Haibing Guo, Cheng-Guo Dong, Dae-Shik Kim, Daisuke Urabe, Jiashi Wang, Joseph T. Kim, Xiang Liu, Takeo Sasaki, and Yoshito Kishi, J. Am. Chem. Soc. 131, 15387 (2009).
- “New Syntheses of E7389 and Halichondrin C14-C38 Building Blocks: Reductive Cyclization and Oxy-Michael Cyclization Approaches”, Cheng-Guo Dong, James A. Henderson, Yosuke Kaburagi, Takeo Sasaki, Dae-Shik Kim, Joseph T. Kim, Daisuke Urabe, Haibing Guo, and Yoshito Kishi, J. Am. Chem. Soc. 131, 15642 (2009).
- “Dramatic Improvement on Catalyst Loadings and Molar Ratios of Coupling Partners for Ni/Cr-Mediated Coupling Reactions: Heterobimetallic Catalysts”, Xiang Liu, James A. Henderson, Takeo Sasaki, and Yoshito Kishi, J. Am. Chem. Soc. 131, 16678 (2009).
- “Total Synthesis of Halichondrin C”, Akihiko Yamamoto, Atsushi Ueda, Paul Brémond, Paolo S. Tiseni, and Yoshito Kishi, J. Am. Chem. Soc. 134, 893 (2012).
- “Photochemistry of Mycolactone A/B, the Causative Toxin of Buruli Ulcer”, Yalan Xing, Sudhir M. Hande, and Yoshito Kishi, J. Am. Chem. Soc. 134, 19234 (2012).