論文

 

原著論文

2020

  1. 1.Synthesis of the Common Monomeric Unit of Uroleuconaphins and Viridaphins via Hauser–Kraus Annulation Kitamura, K,; Kanagawa, H.; Ozakai, C.; Nishimura, T.; Tokuda, H.; Tsunoda, T.; Kaku, H. SYNTHESIS, accepted.

  2. 2.Total Syntheses and Cytotoxic Evaluations of Cryptolactones A1, A2, B1, B2 and Their Derivatives Inai, M,; Oguri, Y.; Horikawa, M.; Kaku, H.; Suzuki, S.; Kitamura, K.; Tsunoda, T. Chem. Pharm. Bull 2020, 68 (4), 380-383. DOI: 10.1248/cpb.c19-01114 ←Featured Articleに選ばれました！！


2019

  1. 1.Piperidine and Azetidine Formation by Direct Cyclization of Diols with N-Nonsubstituted Sulfonamide under The Mitsunobu Conditions Utilizing (Cyanomethylene)Tributylphosphorane (CMBP) and Its Application to The Synthesis of Lupinine Kaku, H.; Sonoda, Y.; Hishida, H.; Taniguchi, Y.; Kubo, A.; Hamaguchi, T.; Horikawa, M.; Inai, M,; Kitamura, K.; Tsunoda, T. Heterocycles 2019, 98 (11),1525-1535. DOI:10.3987/COM-19-14171


2018

  1. 1.Optically Active 2,7,10,15-Tetrahydroxytetraphenylene: Clathrates with Both Enantiomers of 1-Phenylethylamine and Their Stability Kaku, H.; Mitarai, A.; Okamoto, N.; Tanaka, K.; Ichikawa, S.; Yamamoto, T.; Inai, M,; Nishii, T.; Horikawa, M.; Tsunoda, T. Eur. J. Org. Chem. 2018, 48, 6991-6999. DOI:ejoc.201801422

  2. 2.A role of uroleuconaphins, polyketide red pigments in phid, as a chemopreventor in the host defense system against infection with entomopathogenic fungi Horikawa, M.; Shimazu, M.; Aibe, M.; Kaku, H.; Inai, M.; Tsunoda, T. J. Antibiotics. 2018, 71,　992-999. DOI:10.1038/s41429-018-0093-4

  3. 3.3,3-Dimethoxypropylsulfonyl Group: A New Versatile Protecting and Activating Group for Amine Synthesis Sakamoto, I.; Iwaoka, K.; Kawada, Y.; Makida, K.; Takeuchi, Y.; Nishii, T.; Horikawa, M.; Kaku, H.; Tsunoda, T. Tetrahedron. 2018, 74(24), 3052-3060. DOI:10.1016/j.tet.2018.04.088

  4. 4.Ameliorating effects of D-47, a newly developed compound, on lipid metabolism in an animal model of familial hypercholesterolemia (WHHLMI rabbits) Tamura, S.; Koike, Y.; Takeda, H.; Koike, T.; Izumi, Y.; Nagasaka, R.; Tsunoda, T.; Tori, M.; Ogawa, K.; Bamba, T.; Shiomi, M. Eur. J. Pharmacol. 2018, 822 (5), 147-153. DOI:10.1016/j.ejphar.2018.01.013

  5. 5.Deracemization of a-Monosubstituted Cyclopetanone in the presence of a TADDOL-type Host Molecule Kaku, H.; Ito, M.; Horikawa, M; Tsunoda, T. Tetrahdron 2018, 74(1), 124-129. DOI:10.1016/j.tet.2017.11.045


2014

  1. 1.Isolation and Total Syntheses of Cytotoxic Cryptolactones A1, A2, B1, and B2: α,β-Unsaturated δ-Lactones from a Cryptomyzus sp. Aphid Horikawa, M.; Inai, M.; Oguri, Y.; Kuroda, E.; Tanaka, M.; Suzuki, S.; Ito, T.; Takahashi, S.; Kaku, H.; Tsunoda, T. J. Nat. Prod. 2014, 77(11), 2459-2464. DOI: 10.1021/np500542x


2013

  1. 1.A Method to Prepare Optically Active Acyclic alpha-Benzylketones by Thermodynamically Controlled Deracemization Kaku, H.; Imai, T.; Kondo, R.; Mamba, S.; Watanabe, Y.; Inai, M.; Nishii, T.; Horikawa, M.; Tsunoda, T. Eur. J. Org. Chem 2013, 36, 8208-8213. DOI: 10.1002/ejoc.201300936

  2. 2.Xanthouroleuconaphin: a yellowish pigment from the aphid Uroleucon nigrotuberculatum and its total synthesis Nishimura, T.; Horikawa, M.; Yamada, K.; Sogabe, A.; Nishii, T.; Kaku, H.; Inai, M.; Tanaka, M.; Takahashi, S.; Tsunoda, T. Tetrahedron 2013, 69, 1808-1814. DOI: 10.1016/j.tet.2012.12.070 ←Natural Product Updates (66367)


2012

  1. 1.Modified Marko’s aerobic oxidation of alcohols under atmospheric pressure with air or molecular oxygen at room temperature Nishii, T.; Ouchi, T.; Matsuda, A.; Matsubara, Y.; Haraguchi, Y.; Kawano, T.; Kaku, H.; Horikawa, M.; Tsunoda, T. Tetrahedron Lett 2012, 53, 5880-5882. DOI: 10.1016/j.tetlet.2012.08.095 ←Natural Product Updates (65468)

  2. 2.Total Synthesis of Yellowish Aphid Pigment Furanaphin through Fries Rearrangement Assisted with Boron Trifluoride-Acetic Acid Complex Nishimura, T.; Iwata, T.; Maegawa, H.; Nishii, T.; Matsugasako, M.; Kaku, H.; Horikawa, M.; Tsunoda, T. Synlett 2012, 23, 1789-1792. DOI: 10.1055/s-0031-1290429

  3. 3.Construction of an Asymmetric Quaternary Carbon by Asymmetric Aza-Claisen Rearrangement and its Application to a Total Synthesis of (+)-alpha-Cuparenone Nishii, T.; Miyamae, F.; Yoshizuka, M.; Kaku, H.; Horikawa, M.; Inai, M.; Tsunoda, T. Tetrahedron; Asymmetry 2012, 23, 739-741. DOI: 10.1016/j.tetasy.2012.05.016 ←Natural Product Updates (65038)

  4. 4.Megouraphin Glucoside: Two Yellowish Pigments from the Aphid Megoura crassicauda Mordvilko Horikawa, M.; Kikuchi, D.; Imai, T.; Tanaka, M.; Kaku, H.; Nishii, T.; Inai, M.; Takahashi, S.; Tsunoda, T. Heterocycles 2012, 85(1), 95-101. DOI: 10.3987/COM-11-12369 ←Natural Product Updates (64377)


2011

  1. 1.Promotion of Asymmetric Aza-Claisen Rearrangement of N-Allylic Carboxamides Using Excess Base Yoshizuka, M.; Nishii, T.; Sasaki, H.: Kitakado, J.; Ishigaki, N.; Okugawa, S.; Kaku, H.; Horikawa, M.; Inai, M.; Tsunoda, T. Synlett 2011, 20, 2967-2970. DOI: 10.1055/s-0031-1289899

  2. 2.Viridaphin A1 Glucoside, a Green Pigment Possessing Cytotoxicity and Antibacterial Activity from the Aphid Megoura crassicauda Mordvilko Horikawa, M.; Hoshiyama, T.; Matsuzawa, M.; Shugyo, T.; Tanaka, M.; Suzuki, S.; Sato, M.; Ito, T.; Asakawa, Y.; Kaku, H.; Nishii, T.; Inai, M.; Takahashi, S.; Tsunoda, T. J. Nat. Prod. 2011, 74(8), 1812-1816. DOI: 10.1021/np2001286

  3. 3.Total Synthesis of (+)-Brefeldin C utilizing aza-Claisen Rearrangement Inai, M.; Nishii, T.; Mukoujima, S.; Esumi, T.; Kaku, H.; Tominaga, K.; Abe, H.; Horikawa, M.; Tsunoda, T. Synlett 2011, 10, 1459-1461. DOI: 10.1055/s-0030-1260762 ←Natural Product Updates (63061)

  4. 4.Total Synthesis of the (+)-Antimycin A Family Inai, M.; Nishii, T.; Tanaka, A.: Kaku, H.; Horikawa, M.; Tsunoda, T. Eur. J. Org. Chem 2011, 14, 2719-2729. DOI: DOI: 10.1002/ejoc.201100034 ←Natural Product Updates (62941)


2010

  1. 1.Symbiotic Bacterium Modifies Aphid Body Color Tsuchida, T.; Koga, R.; Horikawa, M.; Tsunoda, T.; Maoka,T.; Matsumoto, S.; Simon, J.-C.; Fukatsu, T. Science 2010, 330(6007), 1102-1104. DOI: 10.1126/science.1195463

  2. 2.A Facile and Practical Method of Preparing Optically Active alpha-Monosubstituted Cycloalkanones by Thermodynamically Controlled Deracemization Kaku, H.; Nakamaru, A.; Inai, M.; Nishii, T.; Horikawa, M.; Tsunoda, T. Tetrahedron 2010, 66(48), 9450-9455. DOI: 10.1016/j.tet.2010.09.085

  3. 3.Enantioselective Total Synthesis of (R)-alpha-Lipoic Acid: An Application of Thermodynamically Controlled Deracemization of (±)-2-(2-Methoxyethyl)cyclohexanone  Kaku, H.; Okamoto, N.; Nishii, T.; Horikawa, M.; Tsunoda, T. SYNTHESIS 2010, 17(10), 2931-2934. DOI: 10.1055/s-0030-1258167


2008

  1. 1.Uroleuconaphins A2a, A2b, B2a, and B2b: four yellowish pigments from the aphid Uroleucon nigrotuberculatum (Olive). Horikawa, M.; Tanaka, M.; Kaku, H.; Nishii, T.; Tsunoda, T. Tetrahedron 2008, 64(23),  5515-5518. DOI: 10.1016/j.tet.2008.03.100 ←Natural Product Updates (56153)


2007

  1. 1.A practical total synthesis of (+)-antimycin A9. Nishii, T.; Inai, M.; Kaku, H.; Horikawa, M.; Tsunoda, T. J. Antibiot. 2007, 60(1), 65-72. DOI: 10.1038/ja.2007.9


2006

  1. 1.2-(1,3-Dioxan-2-yl)ethylsulfonyl Group: A New Versatile Protecting and Activating Group for Amine Synthesis. Sakamoto, I.; Izumi, N.; Yamada, T.; Tsunoda, T. Org. Lett. 2006, 8(1), 71-74. DOI: 10.1021/ol052545+

  2. 2.Uroleuconaphins A1 and B1, two red pigments from the aphid Uroleucon nigrotuberculatum (Olive). Horikawa, M.; Hashimoto, T.; Asakawa, Y.; Takaoka, S.; Tanaka, M.; Kaku, H.; Nishii, T.; Yamaguchi, K.; Masu, H.; Kawase, M.; Suzuki, S.; Sato, M.; Tsunoda, T. Tetrahedron 2006, 62(38), 9072-9076. DOI: 10.1016/j.tet.2006.06.111 ←Natural Product Updates (51686)

  3. 3.Pigments from Uroleucon nigrotuberculatum induce apoptosis in HL60 human leukemia cells, implicating intracellular oxidative stress and activation of caspases. Suzuki, S.; Tomita, M.; Hyodo, M.; Horikawa, M.; Tsunoda, T.; Sato, M. Biol. Pharm. Bull. 2006, 29(12), 2383-2387. DOI: 10.1248/bpb.29.2383


2005

  1. 1.Preparation of (Cyanomethylene)tributylphosphorane: A new Mitsunobu-type reagent. Sakamoto, I.; Nishii, T.; Ozaki, F.; Kaku, H.; Tanaka, M.; Tsunoda, T. Chem. Pharm. Bull. 2005, 53(11), 1508-1509. DOI: 10.1248/cpb.53.1508

  2. 2.Heteroatom-Guided Torquoselective Olefination of α-Oxy and α-Amino Ketones via Ynolates. Shindo, M.; Yoshikawa, T.; Itou, Y.; Mori, S.; Nishii, T.; Shishido, K. Chem. Eur. J. 2005, 12, 524-536.  DOI: 10.1002/chem.200500574


2004

  1. 1.Furanaphin: a novel naphtho[2,3-c]furan-4(1H)-one derivative from the aphid Aphis spiraecola Patch. Horikawa, M.; Noguchi, T.; Takaoka, S.; Kawase, M.; Sato, M.; Tsunoda, T. Tetrahedron 2004, 60(5), 1229-1234. DOI: 10.1016/j.tet.2003.11.061,←Natural Product Updates (45806)

  2. 2.A modified thermodynamically controlled deracemization of 2-allylcyclohexanone and its application to asymmetric synthesis of (R)-(-)-epilachnene. Kaku, H.; Okamoto, N.; Nakamaru, A.; Tsunoda, T. Chem. Lett. 2004, 33(5), 516-517. DOI:10.1246/cl.2004.516　←Natural Product Updates (46840)


2003

  1. 1.Preparation of (cyanomethylene)trimethylphosphorane as a new Mitsunobu-type reagent. Sakamoto, I.; Kaku, H.; Tsunoda, T. Chem. Pharm. Bull. 2003, 51(4), 474-476. DOI: 10.1248/cpb.51.474 ←Methods in Organic Synthesis (52182)

  2. 2.Total synthesis of the (+)-antimycin A3 family: structure elucidation of (+)-antimycin A3a. Nishii, T.; Suzuki, S.; Yoshida, K.; Arakaki, K.; Tsunoda, T. Tetrahedron Lett. 2003, 44(42), 7829-7832. DOI: 10.1016/j.tetlet.2003.08.046 ←Natural Product Updates (44958)


2002

  1. 1.The nature of the thermodynamically controlled deracemization of 2-benzylcyclohexanone using (R,R)-(-)-trans-2,3-bis(hydroxydiphenylmethyl)-1,4-dioxaspiro[5.4]decane (TADDOL) : a crystallographic result of inclusion complex. Kaku, H.; Takaoka, S.; Tsunoda, T. Tetrahedron 2002, 58(17), 3401-3407. DOI: 10.1016/S0040-4020(02)00281-8


2001

  1. 1.Prenyl and geranyl phenyl sulfone, a new carbon nucleophile for Mitsunobu-type alkylation. Uemoto, K.; Kawahito, A.; Matsushita, N.; Sakamoto, I.; Kaku, H.; Tsunoda, T. Tetrahedron Lett. 2001, 42(5), 905-907. DOI: 10.1016/S0040-4039(00)02129-8 ←Methods in Organic Synthesis (45893)

  2. 2.Thermodynamically controlled deracemization of 2-alkylcycloalkanones utilizing host-guest inclusion complexation. Kaku, H.; Ozako, S.; Kawamura, S.; Takatsu, S.; Ishii, M.; Tsunoda, T. Heterocycles 2001, 55(5), 847-850. DOI: 10.3987/COM-01-9179


2000

  1. 1.A total synthesis of (-)-antimycin A3b. Tsunoda, T.; Nishii, T.; Yoshizuka, M.; Yamasaki, C.; Suzuki, T.; Itô, S. Tetrahedron Lett. 2000, 41(40), 7667-7671. DOI: 10.1016/S0040-4039(00)01316-2 ←Natural Product Updates (37045)


1999

  1. 1.A facile one-pot cyanation of primary and secondary alcohols. Application of some new Mitsunobu reagents. Tsunoda, T.; Uemoto, K.; Nagino, C.; Kawamura, M.; Kaku, H.; Itô, S. Tetrahedron Lett. 1999, 40(41), 7355-7358. DOI: 10.1016/S0040-4039(99)01509-9 ←Methods in Organic Synthesis (42166)

  2. 2.Arylmethyl phenyl sulfones, a new carbon nucleophile for Mitsunobu-type alkylation. Tsunoda, T.; Uemoto, K.; Ohtani, T.; Kaku, H.; Itô, S. Tetrahedron Lett. 1999, 40(41), 7359-7362.  DOI: 10.1016/S0040-4039(99)01510-5 ←Methods in Organic Synthesis (42167)

  3. 3.Cyanomethylenetrimethylphosphorane, a powerful reagent for the Wittig olefination of esters, lactones and imides. Tsunoda, T.; Takagi, H.; Takaba, D.; Kaku, H.; Itô, S. Tetrahedron Lett. 1999, 41(2), 235-237. DOI: 10.1016/S0040-4039(99)02054-7 ←Methods in Organic Synthesis (42853)


1998

  1. 1.Mitsunobu type C-N bond formation with 4,7-dimethyl3,5,7-hexahydro-1,2,4,7-tetrazocin-3,8-dione (DHTD), a new cyclic azodicarboxamide. Tsunoda, T.; Kawamura, Y.; Uemoto, K.; Itô, S. Heterocycles 1998, 47(1), 177-179. DOI: 10.3987/COM-97-S(N)78


1997

  1. 1.Deracemization of 2-alkylcyclohexanones utilizing host-guest molecular association with optically active host compounds in basic suspension media. Tsunoda, T.; Kaku, H.; Nagaku, M.; Okuyama, E. Tetrahedron Lett. 1997, 38(44), 7759-7760. DOI: 10.1016/S0040-4039(97)10071-5


1996

  1. 1.Mitsunobu-type alkylation of p-toluenesulfonamide. A convenient new route to primary and secondary amines. Tsunoda, T.; Yamamoto, H.; Goda, K.; Itô, S. Tetrahedron Lett. 1996, 37(14), 2457-8. DOI: 10.1016/0040-4039(96)00317-6

  2. 2.Mitsunobu-type alkylation with active methine compounds. Tsunoda, T.; Nagino, C.; Oguri, M.; Itô, S. Tetrahedron Lett. 1996, 37(14), 2459-62. DOI: 10.1016/0040-4039(96)00318-8

  3. 3.Formation of heterocycles by the Mitsunobu reaction. Stereoselective synthesis of (+)-α-skytanthine. Tsunoda, T.; Ozaki, F.; Shirakata, N.; Tamaoka, Y.; Yamamoto, Hi.; Itô, S. Tetrahedron Lett. 1996, 37(14), 2463-6. DOI: 10.1016/0040-4039(96)00319-X

その他

2019

  1. 1.加来裕人『有機結晶部会ニュースレター』2019, 45, 112（ 特集　有機分子集合体の構造と物性）


2009

  1. 1.加来裕人『有機結晶部会ニュースレター』2009, 24, 53（有機結晶2008年論文集）


2004

  1. 1.西井　健「全合成達成!! その後は…：(＋)‐Migrastatinの構造活性相関」『ファルマシア』2004, 40(10), 941-942（トピックス欄）


2003

  1. 1.加来裕人『有機結晶部会ニュースレター』2003, 13, 76（特集欄　固体反応 ーその化学と物性評価ー）


2002

1. 加来裕人「多様な光学活性β-ラクタム合成法」『ファルマシア』2002, 38(10), 968（トピックス欄）

総説

2009

  1. 1.角田鉄人「光延反応　-アルコールの大変身-」『化学と教育』2009, 57(9), 414-415.


2008

  1. 1.加来裕人「熱力学的な平衡条件下での包接分子認識現象を利用したデラセミ化法の開発」『薬学雑誌』2008, 128(10), 1431. [full article] ← !! BioMedLib Top10 article !!

  2. 2.Tsunoda, T.; Nishii, T.; Sakamoto, I. 2-(1,3-Dioxan-2-yl)ethylsulfonyl Chloride “Encyclopedia of Reagents for Organic Synthesis (e-EROS)” L. Paquette ed., John Wiley & Sons, Ltd, West Sussex, UK. 2008, 14 March.


2005

  1. 1.角田鉄人，加来裕人，坂本　泉「新光延試薬」『ファルマシア』2005, 41(6), 518-522.

  2. 2.Tsunoda, T,; Kaku, H.; Ito, S. New Mitsunobu Reagent. TCIMAIL 2005, 123, 2-11.


2004

  1. 1.角田鉄人，加来裕人「新しい光延試薬」『化学工業』2004, 55(5), 349-353.

  2. 2.角田鉄人，加来裕人，伊東　椒「新光延試薬」『TCIメール』2004, 123, 2-15.


2003

  1. 1.Tsunoda, T.; Kaku, H. N,N,N′,N′-Tetramethylazodicarboxamide. “Encyclopedia of Reagents for Organic Synthesis (e-EROS)” L. Paquette ed., John Wiley & Sons, Ltd, West Sussex, UK. 2003, 15 October.

  2. 2.Tsunoda, T. New Redox System for the Mitsunobu Reaction. 『有機合成創造の軌跡-126のマイルストーン- 』有機合成化学協会編，化学同人，2003, 232-233.


1999

  1. 1.Itô, S.; Tsunoda, T. New Mitsunobu reagents in the C-C bond formation. Application to natural product synthesis. Pure Appl. Chem. 1999, 71(6), 1053-1057.


1997

  1. 1.角田鉄人，伊東　椒「新しい光延試薬の創製」『有機合成化学会誌（J. Synth. Org. Chem. Jp）』1997, 55(7), 631-641.