Publications 1996~2018 (Tsunoda Lab.)
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2018
Optically Active 2,7,10,15-Tetrahydroxytetraphenylene: Clathrates with Both Enantiomers of 1-Phenylethylamine and Their Stability
Hiroto Kaku, Akinobu Mitarai, Natsuko Okamoto, Kenta Tanaka, Sayaka Ichikawa, Takahiro Yamamoto, Makoto Inai, Takeshi Nishii, Mitsuyo Horikawa, Tetsuto Tsunoda
Eur. J. Org. Chem., 2018, 48, 6991-6999. DOI:ejoc.201801422
A role of uroleuconaphins, polyketide red pigments in aphid, as a chemopreventor in the host defense system against infection with entomopathogenic fungi
Mitsuyo Horikawa, Mitsuaki Shimazu, Maki Aibe, Hiroto Kaku, Makoto Inai, Tetsuto Tsunoda
J. Antibiotics, 2018, 71, 992–999. DOI:10.1038/s41429-018-0093-4
3,3-Dimethoxypropylsulfonyl Group: A new versatile protecting and activating group for amine synthesis
Izumi Sakamoto, Kazuya Iwaoka, Yuta Kawada, Takanori Naito, Kazuyoshi Makida, Yuki Takeuchi, Takeshi Nishii, Mitsuyo Horikawa, Hiroto Kaku, Tetsuto Tsunoda
Tetrahedron, 2018, 74 (24), 3052-3060. DOI:10.1016/j.tet.2018.04.088
Deracemization of α-monosubstituted cyclopentanones in the presence of a TADDOL-type host molecule
Hiroto Kaku, Minami Ito, Mitsuyo Horikawa, Tetsuto Tsunoda
Tetrahedron, 2018, 74 (4), 124-129. DOI:10.1016/j.tet.2017.11.045
2014
Isolation and Total Syntheses of Cytotoxic Cryptolactones A1, A2, B1, and B2: α,β-Unsaturated δ-Lactones from a Cryptomyzus sp. Aphid. Mitsuyo Horikawa, Makoto Inai, Yuki Oguri, Eri Kuroda, Masami Tanaka, Shinya Suzuki, Takuya Ito, Shigeru Takahashi, Hiroto Kaku, Tetsuto Tsunoda J. Nat. Prod. 2014, 77 (11), 2459-2464. DOI: 10.1021/np500542x
2013
A Method to Prepare Optically Active Acyclic alpha-Baenzylketones by Thermodynamically Controlled Deracemization. Hiroto Kaku, Takahiro Imai, Risa Kondo, Shiho Mamba, Yu Watanabe, Makoto Inai, Takeshi Nishii, Mitsuyo Horikawa, Tetsuto Tsunoda. Eur. J. Org. Chem 2013, 36, 8208-8213. DOI: 10.1002/ejoc.201300936
Xanthouroleuconaphin: a yellowish pigment from the aphid Uroleucon nigrotuberculatum and its total synthesis. Taichi Nishimura, Mitsuyo Horikawa, Kouji Yamada, Ayaka Sogabe, Takeshi Nishii, Hiroto Kaku, Makoto Inai, Masami Tanaka, Shigeru Takahashi, Tetsuto Tsunoda. Tetrahedron 2013, 69, 1808-1814. DOI: 10.1016/j.tet.2012.12.070. Natural Product Updates (66367) に掲載
2012
Modified Marko’s aerobic oxidation of alcohols under atmospheric pressure with air or molecular oxygen at room temperature. Takeshi Nishii, Tomomi Ouchi, Aya Matsuda, Yuka Matsubara, Yuko Haraguchi, Tomomi Kawano, Hiroto Kaku, Mitsuyo Horikawa, Tetsuto Tsunoda. Tetrahedron Lett 2012, 53, 5880-5882. DOI: 10.1016/j.tetlet.2012.08.095 Natural Product Updates (65468)に掲載
Total Synthesis of Yellowish Aphid Pigment Furanaphin through Fries Rearrangement Assisted with Boron Trifluoride-Acetic Acid Complex. Taichi Nishimura, Takeki Iwata, Hironori Maegawa, Takeshi Nishii, Masami Matsugasako, Hiroto Kaku, Mitsuyo Horikawa, Tetsuto Tsunoda. Synlett 2012, 23, 1789-1792. DOI: 10.1055/s-0031-1290429
Construction of an Asymmetric Quaternary Carbon by Asymmetric Aza-Claisen Rearrangement and its Application to a Total Synthesis of (+)-alpha-Cuparenone. Takeshi Nishii, Fumiaki Miyamae, Makoto Yoshizuka, Hiroto Kaku, Mitsuyo Horikawa, Makoto Inai, Tetsuto Tsunoda. Tetrahedron; Asymmetry 2012, 23, 739-741. DOI: 10.1016/j.tetasy.2012.05.016. Natural Product Updates (65038)に掲載
Megouraphin Glucoside: Two Yellowish Pigments from the Aphid Megoura crassicauda Mordvilko. Mitsuyo Horikawa, Daisuke Kikuchi, Toshihito Imai, Masami Tanaka, Hiroto Kaku, Takeshi Nishii, Makoto Inai, Shigeru Takahashi, Tetsuto Tsunoda. Heterocycles 2012, 85(1), 95-101. DOI: 10.3987/COM-11-12369. Natural Product Updates (64377)に掲載
2011
Promotion of Asymmetric Aza-Claisen Rearrangement of N-Allylic Carboxamides Using Excess Base. Makoto Yoshizuka, Takeshi Nishii, Hiromi Sasaki, Junko Kitakado, Noriko Ishigaki, Shinobu Okugawa, Hiroto Kaku, Mitsuyo Horikawa, Makoto Inai, Tetsuto Tsunoda. Synlett 2011, 20, 2967-2970. DOI: 10.1055/s-0031-1289899
Viridaphin A1 Glucoside, a Green Pigment Possessing Cytotoxicity and Antibacterial Activity from the Aphid Megoura crassicauda Mordvilko. Mitsuyo Horikawa, Tosho Hoshiyama, Masami Matsuzawa, Takanori Shugyo, Masami Tanaka, Shinya Suzuki, Masao Sato, Takuya Ito, Yoshinori Asakawa, Hiroto Kaku, Takeshi Nishii, Makoto Inai, Shigeru Takahashi, Tetsuto Tsunoda. J. Nat. Prod. 2011, 74(8), 1812-1816. DOI: 10.1021/np2001286
Total Synthesis of (+)-Brefeldin C utilizing aza-Claisen Rearrangement. Makoto Inai, Takeshi Nishii, Shingo Mukoujima, Tomoyuki Esumi, Hiroto Kaku, Keiko Tominaga, Hiroaki Abe, Mitsuyo Horikawa, Tetsuto Tsunoda. Synlett 2011, 10, 1459-1461. DOI: 10.1055/s-0030-1260762. Natural Product Updates (63061)に掲載
Total Synthesis of the (+)-Antimycin A Family. Makoto Inai, Takeshi Nishii, Ayako Tanaka, Hiroto Kaku, Mitsuyo Horikawa, Tetsuto Tsunoda. Eur. J. Org. Chem 2011, 14, 2719-2729. DOI: 10.1002/ejoc.201100034. Natural Product Updates (62941)に掲載
2010
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
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
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
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)に掲載
2007
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
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+
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)に掲載
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
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
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
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)に掲載
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)に掲載
2003
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)に掲載
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)に掲載
2002
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
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)に掲載
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
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)に掲載
1999
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)に掲載
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)に掲載
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)に掲載
1998
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
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
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
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
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
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