Takeo Sakai, Ph.D. (Associate Professor)

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Name

Takeo Sakai, Ph.D.

 

Address

Faculty of Pharmacy, Meijo University, 150 Yagotoyama,

Tempaku-ku, Nagoya 468-8503, Japan

TEL：+81-52-839-2659

FAX：+81-52-834-8090

E-mail：sakait

(Please add “@meijo-u.ac.jp”)

ORCID: https://orcid.org/0000-0002-9006-8249


Education

March, 2003　B.S. Faculty of Pharmaceutical Sciences, Kyoto University

March, 2005　M.S. Graduate School of Pharmaceutical Sciences, Kyoto University (Prof. Kiyoshi Tomioka)

March, 2008　Ph.D. Graduate School of Pharmaceutical Sciences, Kyoto University (Prof. Kiyoshi Tomioka)


Fellowship

April, 2007 - March, 2009　Research Fellowship of the Japan Society for the Promotion of Science (JSPS) for Young Scientists


Job History

April, 2008 - March, 2010　Postdoctoral Fellow, Department of Chemistry, Massachusetts Institute of Technology (Prof. Rick L. Danheiser)

April, 2010 - March, 2016   Assistant Professor, Faculty of Pharmacy, Meijo University

April, 2016 - Current          Associate Professor, Faculty of Pharmacy, Meijo University


Publications

(Mori’s lab April 2010 - Current, Associate Professor)

  Original papers

  1. 1.Sakai, T.; Takenaka, R.; Koike, Y.; Hira, A.; Mori, Y. p-Methoxy- and 2,4-dimethoxybenzyl N-acetylcarbamate potassium salts: Versatile reagents for N-alkylacetamide and p-methoxy- and 2,4 dimethoxybenzyl carbamates. Chem. Pharm. Bull. accepted.

  2. 2.Sakai, T.; Mizuno, S.; Sone, A.; Hori, Y.; Yamazaki, W.; Takazawa, K.; Mori, Y. Biomimetic construction of a syn-2,7-dimethyloxepane ring via 7-endo cyclization. J. Org. Chem. 2022, 87, 579–594.

  3. 3.Sakai, T.; Okumura, C.; Futamura, M.; Noda, N.; Nagae, A.; Kitamoto, C.; Kamiya, M.; Mori, Y. Gold(I)-Catalyzed Cyclization−3-Aza-Cope−Mannich Cascade and Its Application to the Synthesis of Cephalotaxine. Org. Lett. 2021, 23, 4391–4395.

  4. 4.Sakai, T.; Hata, K.; Kitamura, Y.; Ishibashi, R.; Mori, Y. Synthesis of the ABCD fragment of gymnocin-B. Tetrahedron Lett. 2019, 60, 151261.

  5. 5.Sakai, T.; Sakakibara, H.; Omoto, Y.; Tsunekawa, M.; Hadano, Y.; Kato, S.; Mori, Y. Synthesis of the GHIJKL Fragment of Gymnocin-B. Org. Lett. 2019, 21, 6864–6868.

  6. 6.Sakai, T.; Tatematsu, T.; Fukuta, A.; Kasai, S.; Hayashi, K.; Mori, Y. Benzyl Acetylcarbamate Potassium Salt (BENAC-K): A Simple Nucleophilic N-Acetamide Equivalent. Synthesis 2019, 51, 3638–3650.

  7. 7.Sakai, T.; Noda, N.; Fujimoto, C.; Ito, M.; Takeuchi, H.; Nishiwaki, M.; Mori, Y. Ion-Pair Extraction of Quaternary Ammoniums Using Tetracyanocyclopentadienides and Synthetic Application for Complex Ammoniums. Org. Lett. 2019, 21, 3081–3085.

  8. 8.Sakai, T.; Hattori, M.; Tada, A.; Matsuoka, J.; Mori, Y. Nucleophilic Addition to N-Benzoylisoquinolinium Cation Catalyzed by Sodium Tetracyanocyclopentadienides. Heterocycles 2019, 99, 703–715. (Professor Fukuyama’s memorial issue)

  9. 9.Sakai, T.; Aoyama, K.; Oshima, R.; Furukawa, K.; Mori, Y. Stereoinversion of a Tertiary Alcohol on a THP Ring: a Recovery Route to an Intermediate for Gymnocin-A. Heterocycles 2018, 97, 523–540. (Professor Tomioka’s memorial issue)

  10. 10.Sakai, T.; Nagao, Y.; Nakamura, Y.; Mori, Y. Methanolysis of the Cyclic Acetal Function of NanoKid Catalyzed by NanoGoblin, the Pyridinium Salt of Tetracyanocyclopentadienide. ACS Omega 2017, 2, 8543–8549.

  11. 11.Sakai, T.; Ishihara, A.; Mori, Y. Synthesis of the KLMN fragment of gymnocin-A from the FGH fragment. J. Org. Chem. 2017, 82, 3976–3981.

  12. 12.Sakai, T.; Matsuoka, J.; Shintai, M.; Mori, Y. CAr-O Rotamers in 3,3′-disubstituted BINOL esters. J. Org. Chem. 2017, 82, 3276–3283.

  13. 13.Sakai, T.; Fukuta, A.; Nakamura, K.; Nakano, M.; Mori, Y. Total Synthesis of Brevisamide using an Oxiranyl Anion Strategy. J. Org. Chem. 2016, 81, 3799–3808.

  14. 14.Sakai, T.; Bito, M.; Itakura, M.; Sato, H.; Mori, Y. Acceleration of Acid-Catalyzed Hydrolysis in a Biphasic System by Sodium Tetracyanocyclopentadienides. Chem. Pharm. Bull. 2016, 64, 930–934.

  15. 15.Sakai, T.; Matsushita, S.; Arakawa, S.; Mori, K.; Tanimoto, M.; Tokumasu, A.; Yoshida, T.; Mori, Y. Total Synthesis of Gymnocin-A. J. Am. Chem. Soc. 2015, 137, 14513–14516.

  16. 16.Sakai, T.; Matsushita, S.; Arakawa, S.; Kawai, A.; Mori, Y. Synthetic study of gymnocin-A: synthesis of the ABC ring fragment. Tetrahedron Lett. 2014, 55, 6557–6560.

  17. 17.Sakai, T.; Asano, H.; Furukawa, K.; Oshima, R.; Mori, Y. Synthesis of the KLMN Fragment of Gymnocin-A Using Oxiranyl Anion Convergent Methodology. Org. Lett. 2014, 16, 2268–2271.

  18. 18.Sakai, T.; Seo, S.; Matsuoka, J.; Mori, Y. Synthesis of Functionalized Tetracyanocyclopentadienides from Tetracyanothiophene and Sulfones. J. Org. Chem. 2013, 78, 10978–10985..

  19. 19.Sakai, T.; Sugimoto, A.; Tatematsu, H.; Mori, Y. Divergent Synthesis of trans-Fused Polycyclic Ethers by a Convergent Oxiranyl Anion Strategy. J. Org. Chem. 2012, 77, 11177–11191.

  20. 20.Sakai, T.; Ito, S.; Furuta, H.; Kawahara, Y.; Mori, Y. Mechanism of the Regio- and Diastereoselective Ring Expansion Reaction Using Trimethylsilyldiazomethane, Org. Lett. 2012, 14, 4564–4567.

  21. 21.Sakai, T.; Sugimoto, A.; Mori, Y. A Convergent Strategy for the Synthesis of Polycyclic Ethers by Using Oxiranyl Anions, Org. Lett. 2011, 13, 5850–5853.

  Review papers

  1. 22.Sakai, T.; Mori, Y. Strategies for Brevisamide Synthesis, Based on the Method for Constructing the Tetrahydropyranyl Core, Heterocycles, 2017, 95, 81–115


(Danheiser’s lab April 2008 - March 2010, Postdoc)

  1. 1.Sakai, T.; Danheiser, R. L. Cyano Diels-Alder and Cyano Ene Reactions. Applications in a Formal [2 + 2 + 2] Cycloaddition Strategy for the Synthesis of Pyridines.  J. Am. Chem. Soc. 2010, 132, 13203–13205.

  2. 2.Robinson, J. M.; Sakai, T.; Okano, K.; Kitawaki, T.; Danheiser, R. L. Formal [2 + 2 + 2] Cycloaddition Strategy Based on an Intramolecular Propargylic Ene Reaction/Diels-Alder Cycloaddition Cascade.  J. Am. Chem. Soc. 2010, 132, 11039–11041.

  3. 3.Hamzik, P. J.; Goutierre, A.-S.; Sakai, T.; Danheiser, R. L. Aza Diels–Alder Reactions of Nitriles, N,N-Dimethylhydrazones, and Oximino Ethers. Application in Formal [2 + 2 + 2] Cycloadditions for the Synthesis of Pyridines. J. Org. Chem. 2017, 82, 12967–12974.


(Tomioka’s lab April 2002 - March 2008, Undergrad & Grad Student)

  1. 1.Harada, S.; Sakai, T.; Takasu, K.; Yamada, K.; Yamamoto, Y.; Tomoioka, K. Critical profiles of chiral diether-mediated asymmetric conjugate aminolithiation of enoate with lithium amide as a key to the total synthesis of (–)-kopsinine. Tetrahedron 2013, 69, 3264–3273.

  2. 2.General Entry to Asymmetric One-Pot [N + 2 + n] Cyclization for the Synthesis of Three- to Seven-Membered Azacycloalkanes. Harada, S.; Sakai, T.; Takasu, K.; Yamada, K.; Yamamoto, Y.; Tomioka, K. J. Org. Chem. 2012, 77, 7212–7222.

  3. 3.Total Synthesis of (–)-Kopsinine by an Asymmetric One-Pot [N + 2 + 3] Cyclization. Harada, S.; Sakai, T.; Takasu, K.; Yamada, K.; Yamamoto, Y.; Tomioka, K. Chem.—Asian J. 2012, 7, 2196–2198.

  4. 4.Tomioka, K.; Sakai, T.; Ogata, T.; Yamamoto, Y. Aminolithiation of Carbon-Carbon Double Bonds as A Powerful Tool in Organic Synthesis. Pure Appl. Chem. 2009, 81, 247–253.

  5. 5.Suzuki, M.; Kawamoto, Y.; Sakai, T.; Yamamoto, Y.; Tomioka, K. Asymmetric Construction of Quaternary Carbon Centers by Sequential Conjugate Addition of Lithium Amide and in situ Alkylation: Utility in the Synthesis of (–)-Aspidospermidine. Org. Lett. 2009, 11, 653–655.

  6. 6.Sakai, T.; Yamada, K.; Tomioka, K. Base-Induced Sequential Cyclization–Rearrangement of Enantioenriched 3-Aminoalkanoates to Five-and Seven-Membered Lactams. Chem.—Asian J. 2008, 3, 1486–1493.

  7. 7.Sakai, T.; Doi, H.; Tomioka, K. Chiral Ligand-Controlled Asymmetric Conjugate Amination of Enoates with Lithium Mesitylmethyl(trimethylsilyl)amide. Tetrahedron 2006, 62, 8351–8359.

  8. 8.Sakai, T.; Kawamoto, Y.; Tomioka, K. Asymmetric Synthesis of Intermediates for Otamixaban and Premafloxacin by the Chiral Ligand-Controlled Asymmetric Conjugate Addition of a Lithium Amide. J. Org. Chem. 2006, 71, 4706–4709.

  9. 9.Sakai, T.; Doi, H.; Kawamoto, Y.; Yamada, K.; Tomioka, K. Structure Tuning of Lithium Amide for Asymmetric 1,4-Addition to Cinnamate and Subsequent Demasking. Tetrahedron Lett. 2004, 45, 9261–9263.

  10. 10.Doi, H.; Sakai, T.; Yamada, K.; Tomioka, K. N-Allyl-N-tert-butyldimethylsilylamine for Chiral Ligand-Controlled Asymmetric Conjugate Addition to tert-Butyl Alkenoates. Chem. Commun. 2004, 1850–1851.

  11. 11.Doi, H.; Sakai, T.; Iguchi, M.; Yamada, K.; Tomioka, K. Chiral Ligand-Controlled Asymmetric Conjugate Addition of Lithium Amides to Enoates J. Am. Chem. Soc. 2003, 125, 2886–2887.