Publication List (Hirofumi Ueda)


Original Papers

(38) Concise Total Synthesis of (+)-Pleiocarpamine and Convergent Total Syntheses of (+)-Voacalgine A and (+)-Bipleiophylline via an
  Aerobic Oxidative Coupling
   K. Okada, K. Ojima, H. Ueda, H. Tokuyama
   J. Am. Chem. Soc., 145(30), 16337-16343 (2023) (DOI: 10.1021/jacs.3c05811).

 

(37) Synthetic Studies on Cimiciduphytine
   K. Ojima, H. Ueda, H. Tokuyama
 Bull. Chem. Soc. Jpn., 96,(5), 484-495 (2023) (DOI: 10.1246/bcsj.20230054).

 

(36) Iron-Catalyzed Biomimetic Dimerization of Tryptophan-Containing Peptides
   H. Ueda, S. Sato, K. Noda, H. Hakamata, E. Kwon, N. Kobayashi, H. Tokuyama
   Angew. Chem. Int. Ed., 62,(22), e202302404 (2023) (DOI: 10.1002/anie.202302404). Open Access


   

(35) Efficient and Scalable Asymmetric Total Synthesis of (−)-Emetine with Pharmaceutical Grade Quality; First Multigram Scale Synthesis
   M.Yamada, K. Azuma, I. Takizawa, Y. Ejima, M. Yamano, K. Satoh, T. Doi, H. Ueda, H. Tokuyama
   Org. Process Res. Dev., 27, 343-357 (2023) (DOI) (10.1021/acs.oprd.2c00355).

 

(34) Catalytic Enantioselective 5-endo-Bromocycloetherification of Unactivated Cyclic Alkenes
   H. Xiong, K. Okada, K. Yoshida, H. Ueda, H. Tokuyama
   Tetrahedron Lett., 101, 153906 (2022) (DOI: 10.1016/j.tetlet.2022.153906).

 

(33) Construction of Tetrahydroquinolines with Spirocyclic Structures at the 4-Position
   Y. Wakahara, T. Noro, J. Sakata, H. Ueda, H. Tokuyama
  Heterocycles, 105, 438-460 (2022) (DOI:10.3987/COM-22-S(R)16).

 

(32) Total synthesis of (±)-vinoxine: construction of the bridged pyrido[1,2-a]indole skeleton
   via Tf2O-mediated Bischler–Napieralski reaction and stereoselective radical cyclization
   K. Okada, H. Ueda, H. Tokuyama
   Org. Biomol. Chem., 20,5943-5947 (2022) (DOI:10.1039/D2OB00274D).

 

(31) Synthesis of leuconoxine, leuconodine B, and rhazinilam by transformation of melodinine E via 6-hydro-21-dehydroxyleuconolam
   A. Umehara, H. Ueda, H. Tokuyama
   Tetrahedron, 79, 131809-131814 (2021) (DOI: 10.1016/j.tet.2020.131809).

 

(30) Synthesis of substituted anilines via a gold-catalyzed three-component reaction
   H. Ueda, R. Yamamoto, M. Yamaguchi, H. Tokuyama
   Org. Biomol. Chem., 19, 765-769 (2021) (DOI: 10.1039/D0OB02018D). selected as inside fort cover

 

(29) A Concise Enantioselective Total Synthesis of (–)-Deoxoapodine
   K. Yoshida, K. Okada, H. Ueda, H. Tokuyama
   Angew. Chem. Int. Ed., 59, 23089-23093 (2020) (DOI: 10.1002/anie.202010759).

(28) Nitrile Synthesis by Aerobic Oxidation of Primary Amines and in situ Generated Imines from Aldehydes and Ammonium Salt
  with Grubbs Catalyst
   T. Utsumi, K. Noda, D. Kawauchi, H. Ueda, H. Tokuyama
   Adv. Synth. Catal., 362, 3583-3588 (2020) (DOI: 10.1002/adsc.202000663).

(27) Aerobic Dehydrogenation of N-Heterocycles with Grubbs Catalyst: Its Application to
  Assisted-Tandem Catalysis to Construct N-Containing Fused Heteroarenes
   D. Kawauchi, K. Noda, Y. Komatsu, K. Yoshida, H. Ueda, H. Tokuyama
   Chem. Eur. J., 26, 15793-15798 (2020) (DOI:10.1002/chem.202001961). selected as Hot Paper and Frontispiece

 

(26) Identification of Emetine as a Therapeutic Agent for PulmonaryAarterial Hypertension -A Novel Eeffect of an Old Drug-
  MAH Siddique, K. Satoh, R. Kurosawa, N. Kikuchi, M. Elias-Al-Mamun, J. Omura, T. Satoh, M. Nogi, S. Sunamura, S. Miyata,
  H. Ueda, H. Tokuyama, H. Shimokawa
  Arterioscler. Thromb. Vasc. Biol. (2019) (Doi: 10.1161/ATVBAHA.119.313309.).

 

(25) Construction of Indole Structure on Pyrroloindolines via AgNTf2-Mediated Amination/Cyclization Cascade:
   Application to Total Synthesis of (+)-Pestalazine B
   H. Hakamata, H. Ueda, H. Tokuyama
  Org. Lett.,21, 4205-4209 (2019)  (DOI:10.1021/acs.orglett.9b01399).


(24) Synthesis of Propargylic Ethers by Gold-Mediated Reaction of Terminal Alkynes with Acetals
  D. Kawauchi, H. Ueda, H. Tokuyama
  Chem. Pharm. Bull.,67, 872-876 (2019) (DOI: 10.1248/cpb.c19-00322). selected as highlighted paper and cover picture

 

(23) Double Functionalization of Styrenes by Cu-mediated Assisted Tandem Catalysis
  M. Furuta, K. Sugiyama, M. Yamaguchi, H. Ueda, H. Tokuyama
  Eur. J. Org. Chem., 15, 2056-2060 (2019) (DOI: 10.1002/ejoc.201900088).

 

(22) Novel Potent ABCB1 Modulator, Phenethylisoquinoline Alkaloid, Reverses Multidrug Resistance in Cancer Cell
  N. Sugisawa, S. Ohnuma, H. Ueda, M. Murakami, K. Sugiyama, K. Ohsawa, K. Kano, H. Tokuyama, T. Doi, 
  J. Aoki, M. Ishida, K. Kudoh, T. Naitoh, S. V. Ambudkar, M. Unno
  Mol. Pharmaceutics,15, 4021–4030 (2018)  (DOI: 10.1021/acs.molpharmaceut.8b00457)

(21) Synthetic Studies Toward Isoschizogamine: Construction of Pentacyclic Core Structure
  K. Sugimoto, H. Fujiwara, A. Takada, D.-G. Kim, H. Ueda, H. Tokuyama
  Heterocycles,  97, 10280-1049 (2018) (DOI: 10.3987/COM-18-S(T)8).

(20) AgNTf2-Mediated Allylation with Allylsilanes at C3a-Position of Hexahydropyrroloindoles:
  Application to Total Syntheses of Amauromine Alkaloids
  H. Hakamata, S. Sato, H. Ueda, H. Tokuyama
  Org. Lett., 19, 5308–5311 (2017) (DOI: 10.1021/acs.orglett.7b02602)

(19) AgNTf2-Mediated Arylation of Bromopyrroloindolines
  S. Sato, A. Hirayama, T. Adachi, D. Kawauchi, H. Ueda, H. Tokuyama
  Heterocycles, 94, 1940-1957 (2017) (DOI: 10.3987/COM-17-13777)

(18) Total Syntheses of (+)-T988 B and C via AgNTf2-Mediated Coupling of Bromopyrroloindoline with Indole
  S. Sato, A. Hirayama, H. Ueda, H. Tokuyama
  Asian J. Org. Chem., 6, 54-58 (2017)
(DOI: 10.1002/1joc.201600474)

(17) Bioinspired Total Synthesis of the Dimeric Indole Alkaloid (+)-Haplophytine by Direct Coupling and Late-Stage Oxidative Rearrangement
  H. Satoh, K. Ojima, H. Ueda, H. Tokuyama
  Angew. Chem. Int. Ed., 55, 15157-15161 (2016)
(DOI: 10.1002/anie.201609285)

(16) Condensation of Carboxylic Acids with Non-Nucleophilic N-Heterocycles and Anilides Using Boc2O
  A. Umehara, H. Ueda, H. Tokuyama
  J. Org. Chem., 81, 11444-11453 (2016)
(DOI: 10.1021/acs.joc.6b02097)

(15) Convergent Synthesis of 2-Aryl-Substituted Quinolines by Gold-Catalyzed Cascade Reaction
   H. Ueda, M. Yamaguchi, H. Tokuyama
  Chem. Pharm. Bull., 64, 824-829 (2016)
(DOI: 10.1248/cpb.c16-00193)

(14) Structure and biological function of ENPP6, a choline-specific glycerophosphodiester-phosphodiesterase
  J. Morita, K. Kano, K. Kato, H. Takita, H. Sakagami, Y. Yamamoto, E. Mihara, H. Ueda, T. Sato, H. Tokuyama, H. Arai,
  H. Asou, J. Takagi, R. Ishitani, H. Nishimasu, O. Nureki, J. Aoki
  Scientific Reports, 6, 20995 (2016)
(DOI: 10.1038/srep20995)

(13) Total syntheses of codonopsinine and 4-epi-codonopsinine via gold-mediated tandem catalyzed pyrrole synthesis
  M. Yamaguchi, D. Itagaki, H. Ueda, H. Tokuyama
  J. Antibiot.,69, 253-258 (2016)
(DOI: 10.1038/ja.2016.13)

(12) Synthesis of Substituted Quinolizidines via a Gold-Catalyzed Double Cyclization Cascade
  S. Nonaka, K. Sugimoto, H. Ueda, H. Tokuyama
  Adv. Synth. Catal., 358, 380-385 (2016)
(DOI: 10.1002/adsc.201500907)

(11) Total Synthesis of (–)-Isoschizogamine
  A. Takada, H. Fujiwara, K. Sugimoto, H. Ueda, H. Tokuyama
  Chem. Eur. J., 21, 16400-16403 (2015)
(DOI: 10.1002/chem.201503606)

(10) Synthetic studies on lycopodine: construction of hexahydrojulolidine core by intramolecular Mannich reaction
   T. Sato, H. Ueda, H. Tokuyama
  Tetrahedron Lett., 25, 2503-2507 (2014) (DOI: 10.1016/j.tetlet.2014.10.150)

(9)
Auto tandem Catalysis: Synthesis of Pyrroles by Gold-Catalyzed Cascade Reaction
   H. Ueda, M. Yamaguchi, H. Kameya, K. Sugimoto, H. Tokuyama
  Org. Lett., 16, 4948-4951 (2014)
(DOI: 10.1021/ol5024695)

(8) Acetic Acid-Promoted Metal-Free Aerobic Carbon-Carbon Bond Forming Reactions at α-Position of Tertiary Amines
   H. Ueda, K. Yoshida, H. Tokuyama
  
Org. Lett., 16, 4194-4197 (2014) (DOI: 10.1021/ol5018883)

(7) Total Syntheses of Leuconoxine, Leuconodine B, and Melodinine E by Oxidative Cyclic Aminal Formation
  and Diastereoselective Ring-Closing Metathesis
   A. Umehara, H. Ueda, H. Tokuyama
  Org. Lett., 16, 2526-2529 (2014)
(DOI: 10.1021/ol500903e)

(6) Synthetic Studies on Isoschizogamine: Construction of [3.3.1] Bicyclic Aminal Core by Using Oxidative Skeletal Rearrangement
  H. Ueda, A. Takada, H. Tokuyama
  Tetrahedron Lett., 54, 7115-7118 (2013)
(DOI: 10.1016/j.tetlet.2013.10.083)

(5) Protecting-Group-Free Total Synthesis of (–)-Rhazinilam and (–)-Rhazinicine using a Gold-Catalyzed Cascade Cyclization
  K. Sugimoto, K. Toyoshima, S. Nonaka, K. Kotaki, H. Ueda, H. Tokuyama
  Angew. Chem. Int. Ed., 52, 7168-7171 (2013)
(DOI: 10.1002/anie.201303067)

(4) Synthetic Studies on Strictamine: Unexpected Oxidation of Tertiary Amine in Ru-Catalyzed Ring-Closing Olefin Metathesis
  Y. Komatsu, K. Yoshida, H. Ueda, H. Tokuyama
  Tetrahedron Lett., 54, 377-380 (2013) (DOI: 10.1016/j.tetlet.2012.10.129)

(3) Divergent Total Synthesis of (–)-Aspidophytine and its Congeners via Fischer Indole Synthesis
  H. Satoh, H. Ueda, H. Tokuyama
  Tetrahedron, 69, 89-95 (2013) (DOI: 10.1016/j.tet.2012.10.060)

(2) Total Synthesis of (+)-Haplophytine
  H. Ueda, H. Satoh, K. Matsumoto, K. Sugimoto, T. Fukuyama, H. Tokuyama
  Angew. Chem. Int. Ed., 48, 7600-7603 (2009) (DOI: 10.1002/anie.200902192)

(1) Palladium-Catalyzed Coupling Reaction of Propargylic Oxiranes with Arylboronic Acids in Aqueous Media
  M. Yoshida, H. Ueda, M. Ihara
  Tetrahedron Lett., 46, 6705-6708 (2005) (DOI: 10.1016/j.tetlet.2005.07.134)

Reviews

(4) 制御の難しいアミンの酸化をあえて有機合成に利用する
  植田浩史、徳山英利
  化学と教育、65, 190-191 (2017).

(3) 化学合成が老化現象を解明する!?グルコセパンの効率的全合成
  H.Ueda
  Chemistry (Kagaku), 71, 61-62 (2016)

(2) ユズリハが産み出す高度縮環アルカロイド:ダフマニジンEの全合成
  H.Ueda
  Farumashia, 48, 434 (2012)

(1) 現在の有機合成化学をもってしても合成困難な天然物とは?
  二量体型アルカロイド(+)-Haplophytineの全合成
  徳山英利,植田浩史,福山透
  化学と生物,48,450-453 (2010)