教員紹介

塚本 裕一
Tsukamoto Hirokazu

所属・肩書

薬科学科/創薬化学研究室、創薬研究センター(教授)

最終学歴

東京工業大学大学院理工学研究科 博士後期課程修了

取得学位

博士(工学)

所属学会

日本薬学会、日本化学会、アメリカ化学会、有機合成化学協会

現在の専門分野

有機合成化学、触媒反応、天然物化学

現在の研究課題

●不斉触媒反応の開発
●有機触媒を用いた新規変換反応の開発
●高歪み分子の全合成研究

主要研究業績

●パラジウム触媒を用いた新規変換反応の開発
●高度に酸化された天然物の全合成

最近の研究業績

1.Tsukamoto, H.; Nomura, Y.; *Doi, T. First Total Synthesis of Palmarumycin C6 based on Double Oxa-Michael Addition of 1,8-Dihydroxynaphthalene to 3-Bromo-1-indenone. Heterocycles 2019, 99, published on line

2.Tsukamoto, H.; Hanada, S.; Nomura, Y.; *Doi, T. Total Synthesis of Spiromamakone A and Structure Revision of Spiropreussione A. J. Org. Chem. 2018, 83, 9430–9441.

3.Tsukamoto, H.; Nomura, Y.; Fujiwara, K.; Hanada, S.; *Doi, T. Conjugate Addition to Acylketene Acetals Derived from 1,8-Dihydroxynaphthalene and Its Application To Synthesize the Proposed Structure of Spiropreussione A. Org. Lett. 2018, 20, 3140–3143.

4.*Tsukamoto, H.; Ito, K.; Doi, T. Synthesis of multi-substituted dihydrofurans via palladium-catalysed coupling between 2,3-alkadienols and pronucleophiles. Chem. Commun. 2018, 54, 5102–5105.

5.Tsukamoto, H.; Hanada, S.; Kumasaka, K.; Kagaya, N.; Izumikawa, M.; Shin-ya, K.; *Doi, T. Synthesis of Spiromamakone A Benzo Analogues via Double Oxa-Michael Addition of 1,8-Dihydroxynaphthalene. Org. Lett. 2016, 18, 4848–4851.

6.*Tsukamoto, H.; Ikeda, T.; Doi, T. Palladium(II)-Catalyzed Annulation of Alkynes with 2-(Cyanomethyl)phenylboronates Leading to 3,4-Disubstituted 2-Naphthalenamines. J. Org. Chem. 2016, 81, 1733–1745.

7.*Tsukamoto, H.; Kawase, A.; Doi, T. Asymmetric palladium-catalyzed umpolung cyclization of allylic acetate-aldehyde using formate as a reductant. Chem. Commun. 2015, 51, 8027–8030.

8.Fujiwara, K.; Tsukamoto, H.; Izumikawa, M.; Hosoya, T.; Kagaya, N.; Takagi, M.; Yamamura, H.; Hayakawa, M.; *Shin-ya, K.; *Doi, T. Total Synthesis and Structure Determination of JBIR-108 - A 2-Hydroxy-2-(1-hydroxyethyl)-2,3-dihydro-3(2H)-furanone Isolated from Streptomyces gramineus IR087Pi-4. J. Org. Chem. 2015, 80, 114–132.

9.Qiao, Y.; Leber, M. D.; Schirner, K.; Schaefer, K.; Tsukamoto, H.; *Kahne, D.; *Walker, S. Detection of Lipid-Linked Peptidoglycan Precursors by Exploiting an Unexpected Transpeptidase Reaction. J. Am. Chem. Soc. 2014, 136, 14678–14681.

10.Kuriyama, M.; Haruta, K.; Dairaku, T.; Kawamura, T.; Kikkawa, S.; Inamoto, K.; Tsukamoto, H.; Kondo, Y.; Torigoe, H.; Okamoto, I.; Ono, A.; *Morita, E. H.; *Tanaka, Y. Hg2+-trapping beads: Hg2+-specific recognition through thymine-Hg(II)-thymine base paring. Chem. Pharm. Bull. 2014, 62, 709–712.

11.Leber, M. D.; May, J. M.; Meeske, A. J.; Leiman, S. A.; Lupoli, T. J.; Tsukamoto, H.; Losik, R.; Rudner, D. Z.; *Walker, S.; *Kahne, D. Reconstitution of Peptidoglycan Cross-Linking Leads to Improved Fluorescent Probes of Cell Wall Synthesis. J. Am. Chem. Soc. 2014, 136, 10874–10877.

12.*Tsukamoto, H.; Shiraishi, M.; Doi, T. Alternate Mode of Palladium-Catalyzed Alkynyliminium Ion Cyclizations Affording Stereodefined N-Alkyl-3-alkylidenepyrrolidines. Org. Lett. 2013, 15, 5932–5935.

13.Leber, M. D.; Lupoli, T. J.; Tsukamoto, H.; May, J. M.; *Walker, S.; *Kahne, D. Forming Cross-Linked Peptidoglycan from Synthetic Gram-Negative Lipid II. J. Am. Chem. Soc. 2013, 135, 4632–4635.

14.Gampe, C. M.; Tsukamoto, H.; Doud, E. H.; *Walker, S.; *Kahne, D. Tuning the moenomycin pharmacophore to enable discovery of bacterial cell wall synthesis inhibitors. J. Am. Chem. Soc. 2013, 135, 3776–3779.

15.Gampe, C. M.; Tsukamoto, H.; Wang, T.-S. A.; *Walker, S.; *Kahne, D. Modular synthesis of diphospholipid oligosaccharide fragment of the bacterial cell wall and their use to study the mechanism of moenomycin and other antibiotics. Tetrahedron 2011, 67, 9771–9778.

16.Tsukamoto, H.; *Kahne, D. N-Methylimidazolium chloride-catalyzed pyrophosphate formation: Application to the synthesis of Lipid I and NDP-sugar donors. Bioorg. Med. Chem. Lett. 2011, 21, 5050–5053.

17.Lupoli, T. J.; Tsukamoto, H.; Doud, E. H.; Wang, T.-S. A.; *Walker, S.; *Kahne, D. Transpeptidase-Mediated Incorporation of D-Amino Acids into Bacterial Peptidoglycan. J. Am. Chem. Soc. 2011, 133, 10748–10751.

18.Wang, T.-S. A.; Lupoli, T. J.; Sumida, Y.; Tsukamoto, H.; Wu, Y.; Rebets, Y.; *Kahne, D. E.; *Walker, S. Primer Preactivation of Peptidoglycan Polymerases. J. Am. Chem. Soc. 2011, 133, 8528–8530.

19.Fuse, S.; Tsukamoto, H.; Yuan, Y.; Wang, T.-S. A.; Zhang, Y.; Bolla, M.; *Walker, S.; Sliz, P.; *Kahne, D. Functional and Structural Analysis of a Key Region of the Cell Wall Inhibitor Moenomycin. ACS Chem. Biol. 2010, 5, 701–711.

20.*Tsukamoto, H.; Suzuki, R.; Kondo, Y. Traceless solid-phase synthesis of mappicine ketone library via multiple chemoselective palladium-catalyzed reactions on benzenesulfonate linker. Synlett 2008, 2005–2010.

21.*Tsukamoto, H.; Uchiyama, T.; Suzuki, T.; Kondo, Y. Palladium(0)-catalyzed direct cross-coupling reaction of allylic alcohols with aryl- and alkenylboronic acids. Org. & Biomol. Chem. 2008, 6, 3005–3013.

22.*Tsukamoto, H.; Kondo, Y. Palladium(0)-catalyzed alkynyl and allenyl iminium ion cyclizations leading to 1,4-disubstituted 1,2,3,6-tetrahydropyridines. Angew. Chem., Int. Ed. 2008, 47, 4851–4854.

23.*Tsukamoto, H.; Kondo, Y. A New Five-Membered Ring Forming Process Based on Palladium(0)-Catalyzed Arylative Cyclization of Allenyl Enones. Org. Lett. 2008, 10, 2633–2636.

24.*Tsukamoto, H.; Suzuki, T.; Uchiyama, T.; Kondo, Y. Palladium(0)-catalyzed cis-selective alkylative and arylative cyclization of alkynyl enones with organoboron reagents. Tetrahedron Lett. 2008, 49, 4174–4177.

25.*Tsukamoto, H.; Matsumoto, T.; Kondo, Y. Enantioselective Arylative Cyclization of Allenyl Aldehydes with Arylboronic Acids under Pd(II)-diphosphine Catalysis. Org. Lett. 2008, 10, 1047–1050.

26.*Tsukamoto, H.; Matsumoto, T.; Kondo, Y. Microwave-Assisted Palladium(0)-Catalyzed Alkylative Cyclization of Allenyl Aldehydes Leading to 3-Substituted 3-Cycloalken-1-ols. J. Am. Chem. Soc. 2008, 130, 388–389.

27.*Tsukamoto, H.; Suzuki, T.; Kondo, Y. Remarkable solvent effect on Pd(0)-catalyzed deprotection of allyl ethers using barbituric acid derivatives. Synlett 2007, 3131–3136.

28.*Tsukamoto, H.; Suzuki, T.; Sato, M.; Kondo, Y. Chromatography-free Pd-catalyzed deprotection of allyl ethers using PS-DEAM as a scavenger of boronic acids and Pd catalyst. Tetrahedron Lett. 2007, 48, 8438–8441.

29.*Tsukamoto, H.; Kondo, Y. Palladium(II)-Catalyzed Annulation of Alkynes with ortho-Ester-Containing Phenylboronic Acids. Org. Lett. 2007, 9, 4227–4230.

30.*Tsukamoto, H.; Ueno, T.; Kondo, Y. Palladium(0)-Catalyzed Regioselective and Multicomponent Synthesis of 1,2,3-Trisubstituted 1H-Indenes. Org. Lett. 2007, 9, 3033–3036.

受賞

●平成21年 Thieme Chemistry Journal Award 2009
●平成20年 東北大学大学院薬学研究科長賞
●平成19年 日本薬学会東北支部奨励賞「パラジウム触媒反応の酸化的付加の制御と新反応開拓」
●平成18年 万有製薬研究企画賞(有機合成化学協会)「0価パラジウム触媒へのアンチWacker型酸化的付加を利用した新規環状化合物合成法の開発」
●平成15年 コンビナトリアル・ケミストリー研究会研究企画賞(有機合成化学協会)「新規イリジウム・パラジウム触媒反応を鍵反応としたカンプトテシンライブラリーの固相合成研究」

著書及び総説

有機合成実験法ハンドブック第2版 分担執筆(有機合成化学協会編・丸善出版)

入試情報 ADMISSION