Analytical Chemistry (Tanaka Lab.)

Staff

  • Prof.Dr. Yoshiyuki Tanaka
  • Dr. Katsuyuki Nakashima
  • Dr. Yoshikazu Hattori

Research project
Research of our group is mainly focused on the synthetic work of complex natural products, the development of new reactions using radical species, and the isolation and structure determination of natural products.

  1. Synthesis of a sesterterpenoid YW3699 bearing an eight-membered carbocycle using the RCM reaction.
  2. Synthesis of a sesquiterpenoid crispatanolide isolated from the liverwort and the determination of the absolute configuration.
  3. Synthesis of both enantiomers of a sesquiterpenoid bicyclohumulenone isolated from the liverwort for a perfumery usage.
  4. Development of a reductive cyclization reaction to hydrindanone, perhydronaphthalenone, perhydroguaiane, and other bicyclic systems induced by samarium diiodide.
  5. Development of a radical cyclization reaction induced by cerium ammonium nitrate and other radical inducers.
  6. Isolation and structure determination of sesquiterpenoids from Ligularia and related species collected in Hengduang Mountains area and studies on their evolution.
  7. Isolation and structure determination of the chemical constituents in Eupatorium species and studies on genetic correlations.

Publications

  1. M. Tori and M. Sono, Reductive Cyclization Reactions To Bicyclic Compounds Using Samarium Diiodide, Heterocycles, 89, 1369-1391 (2014).
  2. Y. Saito, M. Taniguchi, T. Komiyama, A. Ohsaki, Y. Okamoto, X. Gong, C. Kuroda, M. Tori, Four new compounds from Ligularia virgaurea; isolation of eremophilane and noreremophilane sesquiterpenoids and the absolute configuration of 2a-hydroxyeremophil-11-en-9-one by the CD spectrum and DFT calculation, Tetrahedron69, (2013).
  3. T. Morimitsu, R. Mizutani, K. Nakashima, Y. Saito, M. Tori, Use of RCM Reactions for Construction of Eight-membered Carbocycles and Introduction of a Hydroxy Group at the Juncture Between 5- and 8-membered Carbocycle, Nat. Prod. Commun., 8, (2013).
  4. R. Mizutani, T. Morimitsu, K. Nakashima, M. Tori, Synthesis of a hydrindenone in rings C and D of YW3699, Nat. Prod. Commun., 8, (2013).
  5. K. Nakashima, N. Kikuchi, T. Takehara, T. Shiozawa, S. Takaoka, M. Tori, Synthesis of a key intermediate, 10-acetyl-7-(t-butyldiphenylsilyloxymethyl)-4-methylbicyclo[5.3.0]dec-4-en-1-ol, in the synthesis of pseudolaric acid A, Nat. Prod. Commun., 8, (2013).
  6. Y. Saito, Y. Iwamoto, Y. Okamoto, X. Gong, C. Kuroda, M. Tori, Eight New Alkyne and Alkene Derivatives from Four Saussurea Species Collected in China, Nat. Prod. Commun., 8 (5), 631-634 (2013).
  7. M. Sono, N. Doi, E. Yoshino, S. Onishi, D.Fujii, M. Tori, Samarium (II) Iodide-induced Intermolecular Coupling of a,b-Unsaturated Esters with Ketones. Reactions of Methyl Propiolate and Ethyl Buta-2,3-dienoate with Cyclohexanone and its Application to Synthesis of a Terpene Carboxylic Acid, Tetrahedron Lett., 54, 1947-1950 (2013)
  8. M. Sono, N. Ise, T. Shoji, M. Tori, Cyclization to Hydrindanones with two Methyl Groups at the Juncture Positions Mediated by Samarium Diiodide and Electrolysis, Molecules,17, 11079-11088 (2012).
  9. Y. Saito, Y. Takashima, A. Kamada, Y. Suzuki, M. Suenaga, Y. Okamoto, Y. Matsunaga, R. Hanai, T. Kawahara, X. Gong, M. Tori, C. Kuroda, Chemical and genrtic diversity of Ligularia virgaurea collected in northern Sichuan and adjacent areas of China, Tetrahedron,68, 10011-10029 (2012).
  10. Y. Saito, K. Takiguchi, X. Gong, C. Kuroda, M. Tori, Three new bisabolane-type sesquiterpenoids from Cremanthodiium rhodocephalum (Asteraceae), Heterocycles86, 497-503 (2012).