Publications

(55) The fungal metabolite (+)-terrein abrogates ovariectomy-induced bone loss and receptor activator of nuclear factor-kB ligand-induced osteoclastogenesis by suppressing protein kinase-C alpha/betaII phosphorylation
Kyosuke Sakaida, Kazuhiro Omori*, Masaaki Nakayama, Hiroki Mandai, Saki Nakagawa, Hidefumi Sako, Chiaki Kamei, Satoshi Yamamoto, Hiroya Kobayashi, Satoki Ishii, Mitsuaki Ono, Soichiro Ibaragi, Keisuke Yamashiro, Tadashi Yamamoto, Seiji Suga, Shogo Takashiba
Front. Pharmacol. , in press.

(54) Acylative Desymmetrization of Glycerol Derivatives by Chiral DMAP Derivatives
Hiroki Mandai,* Kosuke Ashihara, Koichi Mitsudo, and Seiji Suga*
Heterocycles 2021, in press.

(53) Kinetic Resolution of Tertiary Alcohols by Chiral DMAP Derivatives: Enantioselective Access to 3-Hydroxy-3-substituted 2-Oxindoles
Hiroki Mandai,* Ryuhei Shiomoto, Kazuki Fujii, Koichi Mitsudo, and Seiji Suga* 
Org. Lett. 202123, 1169.
10.1021/acs.orglett.0c03956

(52) Acylative Desymmetrization of Cyclic meso-1,3-Diols by Chiral DMAP Derivatives
Hiroki Mandai,* Tsubasa Hironaka, Koichi Mitsudo, and Seiji Suga* 
Chem. Lett. 202150, 471.
10.1246/cl.200809

(51) The fungal metabolite (+)-terrein abrogates osteoclast differentiation via suppression of the RANKL signaling pathway through NFATc1
Saki Nakagawa, Kazuhiro Omori,* Masaaki Nakayama, Hiroki Mandai, Satoshi Yamamoto, Hiroya Kobayashi, Hidefumi Sako, Kyosuke Sakaida, Hiroshi Yoshimura, Satoki Ishii, Soichiro Ibaragi, Kimito Hirai, Keisuke Yamashiro, Tadashi Yamamoto, Seiji Suga, and Shogo Takashiba 
Int. Immunopharmacol. 202083, 106429.
10.1016/j.intimp.2020.106429

(50) Electrochemical Synthesis of Thienoacene Derivatives: Transition-Metal-Free Dehydrogenative C−S Coupling Promoted by a Halogen Mediator
Koichi Mitsudo,* Ren Matsuo, Toki Yonezawa, Haruka Inoue, Hiroki Mandai, and Seiji Suga* 
Angew. Chem. Int. Ed. 202059, 7803.
10.1002/anie.202001149

(49) Integrated Synthesis of Thienyl Thioethers and Thieno[3,2-b]thiophenes via 1-Benzothiophen-3(2H)-ones
Koichi Mitsudo,* Nanae Habara, Yoshiaki Kobashi, Yuji Kurimoto, Hiroki Mandai and Seiji Suga*
Synlett 202031, 1947.
10.1055/s-0040-1707280

(48) Iodide-Mediated or Iodide-Catalyzed Demethylation and Friedel–Crafts C–H Borylative Cyclization Leading to Thiophene-Fused 1,2-Oxaborine Derivatives
Keisuke Shigemori, Momoka Watanabe, Julie Kong, Koichi Mitsudo,* Atsushi Wakamiya, Hiroki Mandai, and Seiji Suga* 
Org. Lett. 201921, 2171.
10.1021/acs.orglett.9b00485

(47) 1,10-Phenanthroline- or Electron-Promoted Cyanation of Aryl Iodides
Koichi Mitsudo,* Kazuki Yoshioka, Takayuki Hirata, Hiroki Mandai, Koji Midorikawa, and Seiji Suga*
Synlett 201930, 1209.
10.1055/s-0037-1611793

(46) Enantioselective Acyl Migration Reactions of Furanyl Carbonates with Chiral DMAP Derivatives
Kazuki Fujii, Koichi Mitsudo, Hiroki Mandai,* Toshinobu Korenaga, and Seiji Suga* 
Chem. Eur. J. 201925, 2208.
10.1002/chem.201806050

(45) Fungal metabolite (+)-terrein suppresses IL-6/sIL-6R-induced CSF1 secretion by inhibiting JAK1 phosphorylation in human gingival fibroblasts
Satoshi Yamamoto, Kazuhiro Omori,* Hiroki Mandai, Masaaki Nakayama, Saki Nakagawa, Hiroya Kobayashi, Tadashi Kunimine, Hiroshi Yoshimura, Kyosuke Sakaida, Hidefumi Sako, Soichiro Ibaragi, Tadashi Yamamoto, Hiroshi Maeda, Seiji Suga, and Shogo Takashiba* 
Heliyon 20184, e00979.
10.1016/j.heliyon.2018.e00979

(44) Stereoselective nucleophilic addition reactions to cyclic N-acyliminium ions using the indirect cation pool method: Elucidation of stereoselectivity by spectroscopic conformational analysis and DFT calculations
Koichi Mitsudo, Junya Yamamoto, Tomoya Akagi, Atsuhiro Yamashita, Masahiro Haisa, Kazuki Yoshioka, Hiroki Mandai, Koji Ueoka, Christian Hempel, Jun-ichi Yoshida, and Seiji Suga* 
Beilstein J. Org. Chem. 201814, 1192.
10.3762/bjoc.14.100

(43) Synthesis and Properties of Dithieno-Fused 1,4-Azaborine Derivatives
Koichi Mitsudo,* Keisuke Shigemori, Hiroki Mandai, Atsushi Wakamiya, and Seiji Suga* 
Org. Lett. 201820, 7336.
10.1021/acs.orglett.8b03316

(42) Cu/Fe/O=PPh3-Catalyzed Etherification for the Synthesis of Aryl 3-Benzo[b]thienyl Ethers
Koichi Mitsudo,* Takuya Asada, Tomohiro Inada, Yuji Kurimoto, Hiroki Mandai, and Seiji Suga* 
Chem. Lett. 201847, 1044.
10.1246/cl.180425

(41) Dynamic Kinetic Resolution of Azlactones by a Chiral N,N-Dimethyl-4-aminopyridine Derivative Containing a 1,1ʹ-Binaphthyl Unit: Importance of Amide Groups
Hiroki Mandai,* Kohei Hongo, Takuma Fujiwara, Kazuki Fujii, Koichi Mitsudo, and Seiji Suga* 
Org. Lett. 201820, 4811.
10.1021/acs.orglett.8b01960

(40) Enantioselective Desymmetrization of 1,3-Diols by a Chiral DMAP Derivative
Hiroki Mandai,* Kosuke Ashihara, Koichi Mitsudo, and Seiji Suga* 
Chem. Lett. 201847, 1360.
10.1246/cl.180697

(39) Efficient Synthesis and Properties of [1]Benzothieno[3,2-b]thieno[2,3-d]furans and [1]Benzothieno[3,2-b]thieno[2,3-d]thiophenes
Yuji Kurimoto, Koichi Mitsudo,* Hiroki Mandai, Atsushi Wakamiya, Yasujiro Murata, Hiroki Mori, Yasushi Nishihara, and Seiji Suga* 
Asian J. Org. Chem. 20187, 1635.
10.1002/ajoc.201800270

(38) Rh-Catalyzed Dehydrogenative Cyclization Leading to Benzosilolothiophene Derivatives via Si–H/C–H Bond Cleavage
Koichi Mitsudo,* Seiichi Tanaka, Ryota Isobuchi, Tomohiro Inada, Hiroki Mandai, Toshinobu Korenaga, Atsushi Wakamiya, Yasujiro Murata, and Seiji Suga* 
Org. Lett. 201719, 2564.
10.1021/acs.orglett.7b00878

(37) Synthesis of 3-Benzo[b]thienyl 3-Thienyl Ether via an Addition–Elimination Reaction and Its Transformation to an Oxygen-Fused Dithiophene Skeleton: Synthesis and Properties of Benzodithienofuran and Its π-Extended Derivatives
Koichi Mitsudo,* Yuji Kurimoto, Hiroki Mandai, and Seiji Suga* 
Org. Lett. 201719, 2821.
10.1021/acs.orglett.7b00969

(36) Magnetic Attachment of Lipase Immobilized on Bacteriogenic Iron Oxide Inside a Microtube Reactor for the Kinetic Resolution of Secondary Alcohols
Kyoko Mandai, Takehiro Fukuda, Yuki Miyazaki, Hideki Hashimoto, Hiroki Mandai, Tadashi Ema, Jun Takada, and Seiji Suga* 
Synlett 201728, 805.
10.1055/s-0036-1589953

(35) Desymmetrization of meso-1,2-Diols by a Chiral N,N-4-Dimethylaminopyridine Derivative Containing a 1,1ʹ-Binaphthyl Unit: Importance of the Hydroxy Groups
Hiroki Mandai,* Hiroshi Yasuhara, Kazuki Fujii, Yukihito Shimomura, Koichi Mitsudo, and Seiji Suga* 
J. Org. Chem. 201782, 6846.
10.1021/acs.joc.7b00992

(34) An Intramolecular Nucleophile-Catalyzed Aldol-Lactonization (NCAL) Reaction of S-Aryl-(E)-6-oxohex-2-enethioate with N,N-4-Dimethylaminopyridine N-Oxide
Hiroki Mandai,* Keita Shimowaki, Kohei Hongo, Koichi Mitsudo, and Seiji Suga* 
Heterocycles 201794, 492.
10.3987/COM-16-13614

(33) Hydrogen Bonding-Assisted Enhancement of the Reaction Rate and Selectivity in the Kinetic Resolution of d,l-1,2-Diols with Chiral Nucleophilic Catalysts
Kazuki Fujii, Koichi Mitsudo, Hiroki Mandai,* and Seiji Suga* 
Adv. Synth. Catal. 2017359, 2778.
10.1002/adsc.201700057

(32) Synthetic Terrein Inhibits Progression of Head and Neck Cancer by Suppressing Angiogenin Production
Akane Shibata, Soichiro Ibaragi,* Hiroki Mandai, Toki Tsumura, Koji Kishimoto, Tatsuo Okui, Nur Mohammad Monsur Hassan, Tsuyoshi Shimo, Kazuhiro Omori, Guo-Fu Hu, Shogo Takashiba, Seiji Suga, and Akira Sasaki 
Anticancer Res. 201636, 2161.

(31) Facile Synthesis of Naphthothiophenone Derivatives and Anthradithiophenedione via Friedel–Crafts Acylation and Their Fundamental Properties
Koichi Mitsudo,* Takashi Murakami, Takuya Shibasaki, Tomohiro Inada, Hiroki Mandai, Hiromi Ota, and Seiji Suga* 
Synlett 201627, 2327.
10.1055/s-0035-1562470

(30) Enantioselective acyl transfer catalysis by a combination of common catalytic motifs and electrostatic interactions
Hiroki Mandai,* Kazuki Fujii, Hiroshi Yasuhara, Kenko Abe, Koichi Mitsudo, Toshinobu Korenaga, and Seiji Suga* 
Nat. Commun. 20167, 11297.
10.1038/ncomms11297

(29) Facile Synthesis of 1,4-Bis(diaryl)-1,3-butadiynes Bearing Two Amino Moieties by Electrochemical Reaction-Site Switching and Their Solvatochromic Fluorescence
Natsuyo Kamimoto,* Nariaki Nakamura, Akina Tsutsumi, Hiroki Mandai, Koichi Mitsudo, Atsushi Wakamiya, Yasujiro Murata, Junya Hasegawa, and Seiji Suga* 
Asian J. Org. Chem. 20165, 373.
10.1002/ajoc.201500502

(28) Kinetic Resolution of Secondary Carbinols by a Chiral N,N-4-Dimethylaminopyridine Derivative Containing a 1,1ʹ-Binaphthyl Unit: Hydrogen Bonding Affects Catalytic Activity and Enantioselectivity
Kazuki Fujii, Koichi Mitsudo, Hiroki Mandai,* and Seiji Suga* 
Bull. Chem. Soc. Jpn. 201689, 1081.
10.1246/bcsj.20160135

(27) Synthesis and Properties of Ethene-Bridged Terthiophenes
Koichi Mitsudo,* Hidehiko Sato, Arata Yamasaki, Natsuyo Kamimoto, Jun Goto, Hiroki Mandai, and Seiji Suga* 
Org. Lett. 201517, 4858.
10.1021/acs.orglett.5b02417

(26) Bacteriogenic Iron Oxide as an Effective Catalyst for Baeyer-Villiger Oxidation with Molecular Oxygen and Benzaldehyde
Kyoko Mandai, Minae Hanata, Koichi Mitsudo, Hiroki Mandai, Seiji Suga,* Hideki Hashimoto, and Jun Takada 
Tetrahedron 201571, 9403.
10.1016/j.tet.2015.10.057

(25) Enantioselective Steglich Rearrangement of Oxindole Derivatives by Easily Accessible Chiral N,N-4-(Dimethylamino)pyridine Derivatives
Hiroki Mandai,* Takuma Fujiwara, Katsuaki Noda, Kazuki Fujii, Koichi Mitsudo, Toshinobu Korenaga, and Seiji Suga* 
Org. Lett. 201517, 4436.
10.1021/acs.orglett.5b02089

(24) An Efficient Petasis Boronic–Mannich Reaction of Chiral Lactol Derivatives Prepared from D-Araboascorbic Acid
Hiroki Mandai,* Hiroshi Yamada, Keita Shimowaki, Koichi Mitsudo, and Seiji Suga* 
Synthesis 201446, 2672.
10.1055/s-0034-1378900

(23) Remarkable Enhancement of the Rate of the Intramolecular Morita Baylis-Hillman Reaction by the Combination of a Nucleophilic Catalyst and 1,3-Diphenyl-2-thiourea
Hiroki Mandai,* Keita Shimowaki, Koichi Mitsudo, and Seiji Suga* 
Asian J. Org. Chem. 20143, 437.
10.1002/ajoc.201402001

(22) Synthetic (+)-Terrein Suppresses Interleukin-6/Soluble Interleukin-6 Receptor Induced-Secretion of Vascular Endothelial Growth Factor in Human Gingival Fibroblasts
Hiroki Mandai,* Kazuhiro Omori, Daisuke Yamamoto, Toki Tsumura, Kyouta Murota, Satoshi Yamamoto, Koichi Mitsudo, Soichiro Ibaragi, Akira Sasaki, Hiroshi Maeda, Shogo Takashiba, and Seiji Suga* 
Bioorg. Med. Chem. 201422, 5338.
10.1016/j.bmc.2014.07.047

(21) Electro-Reductive Halogen-Deuterium Exchange and Methylation of Aryl Halides in Acetonitrile
Koichi Mitsudo,* Takahiro Okada, Shuichi Shimohara, Hiroki Mandai, and Seiji Suga* 
Electrochemistry 201381, 362.
10.5796/electrochemistry.81.362

(20) Synthesis of Hexa(furan-2-yl)benzenes and Their P-extended Derivatives
Koichi Mitsudo,* Jyunji Harada, Yo Tanaka, Hiroki Mandai, Chie Nishioka, Hideo Tanaka, Atsushi Wakamiya, Yasujiro Murata, and Seiji Suga* 
J. Org. Chem. 201378, 2763.
10.1021/jo302652r

(19) Recyclable Palladium Catalyst in PEG/CH3CN Biphasic System for Electro-Oxidative Wacker-Type Reaction
Koichi Mitsudo,* Satoshi Fukunaga, Tomoya Fujita, Hiroki Mandai, Seiji Suga, and Hideo Tanaka* 
Electrochemistry 201381, 347.
10.5796/electrochemistry.81.347

(18) Kinetic Resolution of Secondary Alcohols by Chiral DMAP Derivatives Prepared by the Ugi Multicomponent Reaction
Hiroki Mandai,* Shunsuke Irie, Masaru Akehi, Kazunobu Yuri, Masaaki Yoden, Koichi Mitsudo, and Seiji Suga* 
Heterocycles 201387, 329.
10.3987/COM-12-12624

(17) Synthesis of Nitrogen-Bridged Terthiophenes by Tandem Buchwald-Hartwig Coupling and Their Properties
Koichi Mitsudo,* Shuichi Shimohara, Jun Mizoguchi, Hiroki Mandai, and Seiji Suga* 
Org. Lett. 201214, 2702.
10.1021/ol300887t

(16) Site-Selective Sequential Coupling Reactions Controlled by “Electrochemical Reaction Site Switching”: A Straightforward Approach to 1,4-Bis(Diaryl)Buta-1,3-Diynes
Koichi Mitsudo,* Natsuyo Kamimoto, Hiroki Murakami, Hiroki Mandai, Atsushi Wakamiya, Yasujiro Murata, and Seiji Suga* 
Org. Biomol. Chem. 201210, 9562.
10.1039/c2ob26567b

(15) Studies on the Petasis Reaction of 2-Pyridinecarbaldehyde Derivatives and Its Products
Hiroki Mandai,* Kyouta Murota, and Seiji Suga* 
Heterocycles 201285, 1655.
10.3987/COM-12-12500

(14) Kinetic Resolution of Secondary Alcohols by the Combination of a Chiral Brønsted Acid, DABCO, and Acetyl Chloride
Hiroki Mandai,* Kyouta Murota, Koichi Mitsudo, and Seiji Suga* 
Org. Lett. 201214, 3486.
10.1021/ol301373x

(13) Kumada-Tamao-Corriu Coupling Using N-Heterocyclic Carbene Ligands Bearing Pyridyl and Ethylenedioxyl Moieties
Koichi Mitsudo,* Yuta Doi, Syunsuke Sakamoto, Hiroki Murakami, Hiroki Mandai, and Seiji Suga* 
Chem. Lett. 201140, 936.
10.1246/cl.2011.936

(12) Studies on the Synthesis of DMAP Derivatives by Diastereoselective Ugi Reactions
Hiroki Mandai,* Shunsuke Irie, Koichi Mitsudo, and Seiji Suga* 
Molecules 201116, 8815.
10.3390/molecules16108815

(11) Induction of MMP-13 Expression in Bone-metastasizing Cancer Cells by Type I Collagen through Integrin a1b1 and a2b1-p38 MAPK Signaling
Soichiro Ibaragi, Tsuyoshi Shimo,* Nur Mohammad Monsur Hassan, Sachiko Isowa, Naito Kurio, Hiroki Mandai, Shinichi Kodama, and Akira Sasaki 
Anticancer Res. 201131, 1307.

(10) An Improved Protocol for Petasis Reaction of 2-Pyridinecarbaldehydes
Hiroki Mandai,* Kyouta Murota, and Takashi Sakai 
Tetrahedron Lett. 201051, 4779.
10.1016/j.tetlet.2010.07.039

(9) Three-Component Ag-Catalyzed Enantioselective Vinylogous Mannich and Aza-Diels-Alder Reactions with Alkyl-Substituted Aldehydes
Hiroki Mandai, Kyoko Mandai, Marc. L. Snapper,* and Amir. H. Hoveyda* 
J. Am. Chem. Soc. 2008130, 17961.
10.1021/Ja807243t

(8) 6-Nitro-2-Benzothiazolyl a-Mannoside: A Highly Efficient Mannosyl Donor in Constructing b-man(1 -> 4)GlcN Linkage and Its Application to the Synthesis of the Pentasaccharide Core of N-Glycans
Hiroki Mandai, and Teruaki Mukaiyama* 
Bull. Chem. Soc. Jpn. 200679, 479.
10.1246/bscj.79.479

(7) Efficient and Concise Synthesis of bMan1-4GlcN Linkage of Pentasaccharide Core by Using 6-Nitro-2-Benzothiazolyl a-Mannoside
Hiroki Mandai, and Teruaki Mukaiyama* 
Chem. Lett. 200534, 702.
10.1246/cl.2005.702

(6) 6-Nitro-2-Benzothiazolyl a-Glucoside and a-Mannoside in b-Selective Glycosylations
Takashi Hashihayata, Hiroki Mandai, and Teruaki Mukaiyama* 
Bull. Chem. Soc. Jpn. 200477, 169.
10.1246/bcsj.77.169

(5) Glycosyl 6-Nitro-2-Benzothiazoate. A Highly Efficient Donor for b-Stereoselective Glycosylation
Teruaki Mukaiyama,* Takashi Hashihayata, and Hiroki Mandai 
Chem. Lett. 200332, 340.
10.1246/cl.2003.340

(4) Catalytic and b-Stereoselective Mannosylation of Several Glycosyl Acceptors with Mannosyl 6-Nitro-2-Benzothiazoate
Takashi Hashihayata, Hiroki Mandai, and Teruaki Mukaiyama* 
Chem. Lett. 200332, 442.
10.1246/cl.2003.442

(3) A Catalytic and a-Selective Sialylation Using Novel 5-Azido Sialyl Fluoride
Teruaki Mukaiyama,* Hiroki Mandai, and Hideki Jona 
Chem. Lett. 200231, 1182.
10.1246/cl.2002.1182

(2) Protic Acid Catalyzed Stereoselective Glycosylation Using Glycosyl Fluorides
Hideki Jona, Hiroki Mandai, Warinthorn Chavasiri, Kazuya Takeuchi, and Teruaki Mukaiyama* 
Bull. Chem. Soc. Jpn. 200275, 291.
10.1246/bcsj.75.291

(1) A Catalytic and Stereoselective Glycosylation with Glucopyranosyl Fluoride by Using Various Protic Acids
Hideki Jona, Hiroki Mandai, and Teruaki Mukaiyama* 
Chem. Lett. 200130, 426.
10.1246/cl.2001.426