Publications

Original Papers

  1. Y. Yamada, R. Yoshinaga, Y. Matsui, M. Nagatomo, H. Fujino, M. Inoue, “Et3Al/Light-Promoted Radical-Polar Crossover Reactions of α-Alkoxyacyl Tellurides” J. Org. Chem. 2024, 89, 11701–11706.



    DOI: 10.1021/acs.joc.4c01445

  2. A. Watanabe, Y. Hikone, M. Nagatomo, M. Inoue, “Conversion of Phorbol into Des-D-Ring Tricycle and Crotonianoid B via Peroxidation Reaction,” Org. Lett. 2024, 26, 4335–4339.



    DOI: 10.1021/acs.orglett.4c01363

  3. A. Watanabe, M. Nagatomo, A. Hirose, Y. Hikone, N. Kishimoto, S. Miura, T. Yasutake, T. Abe, S. Misumi, M. Inoue, “Total Syntheses of Phorbol and 11 Tigliane Diterpenoids and Their Evaluation as HIV Latency-Reversing Agents,” J. Am. Chem. Soc. 2024, 146, 8746–8756.



    DOI: 10.1021/jacs.4c01589

  4. T. Watanabe, K. Oga, H. Matoba, M. Nagatomo, M. Inoue, “Total Synthesis of Taxol Enabled by Intermolecular Radical Coupling and Pd-Catalyzed Cyclization,” J. Am. Chem. Soc. 2023, 145, 25894–25902.

    (23/12/4 Selected as Most Read Articles)
    (24/1/9 Featured in “Some Items of Interest to Process R&D Chemists and Engineers” Org. Process Res. Dev. 2024, 28, 1.)
    (Featured in Synfacts)



    DOI: 10.1021/jacs.3c10658

  5. Y. Imamura, K. Takaoka, Y. Komori, M. Nagatomo, M. Inoue, “Total Synthesis of Taxol Enabled by Inter- and Intramolecular Radical Coupling Reactions,” Angew. Chem. Int. Ed. 2023, 62, e202219114.

    (Selected as Hot Paper)
    (Featured in Synfacts)



    DOI: 10.1002/anie.202219114

  6. Y. Hikone, T. Kato, M. Nagatomo, M. Inoue, “Total Synthesis of Resiniferatoxin Enabled by Photocatalytic Decarboxylative Radical Cyclization,” Org. Lett. 2022, 24, 929–933.

    (Selected as Most Read Articles)



    DOI: 10.1021/acs.orglett.1c04286

  7. D. Kuwana, Y. Komori, M. Nagatomo, M. Inoue, “Photoinduced Decarboxylative Radical Coupling Reaction of Multiply Oxygenated Structures by Catalysis of Pt-Doped TiO2,” J. Org. Chem. 2022, 87, 730–736.



    DOI: 10.1021/acs.joc.1c02736

  8. A. Hirose, A. Watanabe, K. Ogino, M. Nagatomo, M. Inoue, “Unified Total Syntheses of Rhamnofolane, Tigliane, and Daphnane Diterpenoids,” J. Am. Chem. Soc. 2021, 143, 12387–12396.

    (Featured in Synfacts)
    (Highlighted in Organic Chemistry Highlights)



    DOI: 10.1021/jacs.1c06450

  9. M. Nagatomo, K. Zhang, H. Fujino, M. Inoue, “Et3B/Et2AlCl/O2‐Mediated Radical Coupling Reaction between α‐Alkoxyacyl Tellurides and 2‐Hydroxybenzaldehyde Derivatives,” Chem. Asian. J. 2020, 15, 3820–3824.



    DOI: 10.1002/asia.202001090

  10. T. Fukuda, M. Nagatomo, M. Inoue, “Total Synthesis of Diospyrodin and Its Three Diastereomers,” Org. Lett. 2020, 22, 6468–6472.



    DOI: 10.1021/acs.orglett.0c02280

  11. H. Fujino, T. Fukuda, M. Nagatomo, M. Inoue, “Convergent Total Synthesis of Hikizimycin Enabled by Intermolecular Radical Addition to Aldehyde,” J. Am. Chem. Soc. 2020, 142, 13227–13234.

    (Highlighted in Organic Chemistry Highlights)



    DOI: 10.1021/jacs.0c06354

  12. D. Kuwana, M. Nagatomo, M. Inoue, “Total Synthesis of 5-epi-Eudesm-4(15)-ene-1β,6β-diol via Decarbonylative Radical Coupling Reaction,” Org. Lett. 2019, 21, 7619–7623.



    DOI: 10.1021/acs.orglett.9b02895

  13. Y. Imamura, S. Yoshioka, M. Nagatomo, M. Inoue, “Total Synthesis of 1‐Hydroxytaxinine,” Angew. Chem. Int. Ed. 2019, 58, 12159–12163.

    (Selected as Hot Paper)
    (Highlighted in Organic Chemistry Highlights)



    DOI: 10.1002/anie.201906872

  14. D. Kuwana, B. Ovadia, D. Kamimura, M. Nagatomo, M. Inoue, “Installation of O‐Heterocycles to N‐Heteroarenes via an Et3B/O2‐mediated Radical Reaction of α-Alkoxy and α-Alkoxyacyl Tellurides,” Asian J. Org. Chem. 2019, 8, 1088–1091.



    DOI: 10.1002/ajoc.201900170

  15. M. Nagatomo, Y. Fujimoto, K. Masuda, M. Inoue, “Construction of a 6/5/9-membered tricyclic structure of cladiellins via radical-polar crossover reaction,” J. Antibiot. 2019, 72, 486–489.
    DOI: 10.1038/s41429-019-0150-7

  16. H. Matoba, T. Watanabe, M. Nagatomo, M. Inoue, “Convergent Synthesis of Taxol Skeleton via Decarbonylative Radical Coupling Reaction,” Org. Lett. 2018, 20, 7554–7557.

    (Selected as Most Read Articles of the month)



    DOI: 10.1021/acs.orglett.8b03302

  17. T. Kawamata, A. Yamaguchi, M. Nagatomo, M. Inoue, “Convergent Total Synthesis of Asimicin via Decarbonylative Radical Dimerization,” Chem. Eur. J. 2018, 24, 18907–18912.



    DOI: 10.1002/chem.201805317

  18. D. Urabe, Y. Nakagawa, K. Mukai, K. Fukushima, N. Aoki, H. Itoh, M. Nagatomo, M. Inoue, “Total synthesis and biological evaluation of 19-hydroxysarmentogenin-3-O-a-L-rhamnoside, trewianin, and their aglycons,” J. Org. Chem. 2018, 83, 13888–13910.



    DOI: 10.1021/acs.joc.8b02219

  19. M. Koshimizu, M. Nagatomo, M. Inoue, “Construction of a pentacyclic ring system of isoryanodane diterpenoids by SmI2-mediated transannular cyclization,” Tetrahedron. 2018, 74, 3384–3390.



    DOI: 10.1016/j.tet.2018.03.061

  20. H. Fujino, M. Nagatomo, A. Paudel, S. Panthee, H. Hamamoto, K. Sekimizu, M. Inoue, “Unified Total Synthesis of Polyoxin J, L, and Their Fluorinated Analogues on the Basis of Decarbonylative Radical Coupling Reactions,” Angew. Chem. Int. Ed. 2017, 56, 11865–11869.



    DOI: 10.1002/anie.201706671

  21. K. Masuda, M. Tanigawa, M. Nagatomo, D. Urabe, M. Inoue, “Construction of carbocycles initiated by Cu-catalyzed radical reaction of Cl2C(CN)2,” Tetrahedron 2017, 73, 3596–3605.



    DOI: 10.1016/j.tet.2017.03.063

  22. T. Kawamata, M. Nagatomo, M. Inoue, “Total Synthesis of Zaragozic Acid C: Implementation of Photochemical C(sp3)-H Acylation,” J. Am. Chem. Soc. 2017, 139, 1814–1817.

    (Highlighted in Synfacts 2017, 13, 0337. and selected as its Cover Picture)



    DOI: 10.1021/jacs.6b13263

  23. K. Masuda, M. Nagatomo, M. Inoue, “Direct assembly of multiply oxygenated carbon chains by decarbonylative radical-radical coupling reactions,” Nature Chem. 2017, 9, 207–212.

    (Highlighted in Synfacts 2017, 13, 0534. )
    (Associated Link: News and Views – “Organic chemistry: A radical step forward”)



    DOI: 10.1038/nchem.2639

  24. S. Matsumura, Y. Matsui, M. Nagatomo, M. Inoue, “Stereoselective construction of anti– and syn-1,2-diol structures via decarbonylative radical coupling of α-alkoxyacyl tellurides,” Tetrahedron 2016, 72, 4859–4866.



    DOI: 10.1016/j.tet.2016.06.056

  25. D. Kamimura, M. Nagatomo, D. Urabe, M. Inoue, “Expanding the scope of Et3B/O2-mediated coupling reactions of O,Te-acetal,” Tetrahedron 2016, 72, 7839–7848.



    DOI: 10.1016/j.tet.2016.04.023

  26. K. Masuda, M. Nagatomo, M. Inoue, “Chemical Conversion of Ryanodol to Ryanodine,” Chem. Pharm. Bull. 2016, 64, 874–879.



    DOI: 10.1248/cpb.c16-00214

  27. M. Koshimizu, M. Nagatomo, M. Inoue, “Unified Total Synthesis of 3-epi-Ryanodol, Cinnzeylanol, Cinncassiols A and B, and Structural Revision of Natural Ryanodol and Cinnacasol,” Angew. Chem. Int. Ed. 2016, 55, 2493–2497.



    DOI: 10.1002/anie.201511116

  28. K. Masuda, M. Koshimizu, M. Nagatomo, M. Inoue, “Asymmetric Total Synthesis of (+)-Ryanodol and (+)-Ryanodine,” Chem. Eur. J. 2016, 22, 230–236.



    DOI: 10.1002/chem.201503641

  29. M. Nagatomo, K. Hagiwara, K. Masuda, M. Koshimizu, T. Kawamata, Y. Matsui, D. Urabe, M. Inoue, ” Symmetry-Driven Strategy for the Assembly of the Core Tetracycle of (+)-Ryanodine: Synthetic Utility of a Cobalt-Catalyzed Olefin Oxidation and α-Alkoxy Bridgehead Radical Reaction,” Chem. Eur. J. 2016, 22, 222–229.



    DOI: 10.1002/chem.201503640

  30. M. Nagatomo, D. Kamimura, Y. Matsui, K. Masuda, M. Inoue, “Et3B-Mediated Two- and Three-Component Coupling Reactions via Radical Decarbonylation of α-Alkoxyacyl Tellurides: Single-Step Construction of Densely Oxygenated Carboskeletons,” Chem. Sci. 2015, 6, 2765–2769.



    DOI: 10.1039/C5SC00457H

  31. S. Yoshioka, M. Nagatomo, M. Inoue, “Application of Two Direct C(sp3)-H Functionalizations for Total Synthesis of (+)-Lactacystin,” Org. Lett. 2015, 17, 90–93.



    DOI: 10.1021/ol503291s

  32. M. Nagatomo, H. Nishiyama, H. Fujino, M. Inoue, “Decarbonylative Radical Coupling of α-Aminoacyl Tellurides: Single-Step Preparation of γ-Amino and α,β-Diamino Acids and Rapid Synthesis of Gabapentin and Manzacidin A,” Angew. Chem. Int. Ed. 2015, 54, 1537–1541.

    (Selected as Hot Paper)



    DOI: 10.1002/anie.201410186

  33. M. Nagatomo, S. Yoshioka, M. Inoue, “Enantioselective Radical Alkynylation of C(sp3)-H Bonds Using Sulfoximine as a Traceless Chiral Auxiliary,” Chem. Asian. J. 2015, 10, 120–123.



    DOI: 10.1002/asia.201402983

  34. Y. Amaoka, M. Nagatomo, M. Watanabe, K. Tao, S. Kamijo, M. Inoue, “Photochemically Induced Radical Alkenylation of C(sp3)-H Bonds,” Chem. Sci. 2014, 5, 4339–4345.



    DOI: 10.1039/C4SC01631A

  35. M. Nagatomo, M. Koshimizu, K. Masuda, T. Tabuchi, D. Urabe, M. Inoue “Total Synthesis of Ryanodol,” J. Am. Chem. Soc. 2014, 136, 5916–5919.



    DOI: 10.1021/ja502770n

  36. D. Kamimura, D. Urabe, M. Nagatomo, M. Inoue, “Et3B‐Mediated Radical-Polar Crossover Reaction for Single-Step Coupling of O,Te-Acetal, α,β-Unsaturated Ketones, and Aldehydes/Ketones,” Org. Lett. 2013, 15, 5122–5125.



    DOI: 10.1021/ol402563v

  37. Y. Amaoka, M. Nagatomo, M. Inoue, “Metal-Free Fluorination of C(sp3)-H Bonds Using a Catalytic N-Oxyl Radical,” Org. Lett. 2013, 15, 2160–2163.



    DOI: 10.1021/ol4006757

  38. D. Urabe, M. Nagatomo, K. Hagiwara, K. Masuda, M. Inoue, “Symmetry-Driven Synthesis of 9-Demethyl-10,15-dideoxyryanodol,” Chem. Sci. 2013, 4, 1615–1619.



    DOI: 10.1039/C3SC00023K

  39. M. Nagatomo, T. Nakata, “Stereoselective Synthesis of Maitotoxin GHI-Ring System Having a 1,2-Diol Side Chain,” Heterocycles 2008, 76, 1069–1074.
    DOI: 10.3987/COM-08-S(N)113

Reviews and Accounts

  1. Y. Hikone, M. Nagatomo, M. Inoue, “Development of Streamlined Processes for Construction of Complex Natural Products: Three Synthesis of Resiniferatoxin,” J. Synth. Org. Chem., Jpn. 2023, 81, 1136–1149.


    DOI: 10.5059/yukigoseikyokaishi.81.1136

  2. H. Fujino, M. Nagatomo, M. Inoue, “Total Syntheses of Hikosamine and Hikizimycin,” J. Org. Chem. 2021, 86, 16220–16230.
    (Selected as the cover picture link)



    DOI: 10.1021/acs.joc.1c01773

  3. M. Nagatomo, M. Inoue, “Convergent Assembly of Highly Oxygenated Natural Products Enabled by Intermolecular Radical Reactions,” Acc. Chem. Res. 2021, 54, 595–604.



    DOI: 10.1021/acs.accounts.0c00792

  4. M. Nagatomo, “Development of Synthetic Strategies for Densely Oxygenated Natural Products: Total Synthesis of Lactacystin and Zaragozic Acid C Using Photochemical C(sp3)–H Functionalization,” YAKUGAKU ZASSHI 2019, 139, 651–661.
    DOI: 10.1248/yakushi.18-00210

  5. M. Nagatomo, “Discontent is the First Step in Progress-Learning from the Total Synthesis of Ryanodine,” J. Synth. Org. Chem., Jpn. 2018, 76, 494–497.
    DOI: 10.5059/yukigoseikyokaishi.76.494

  6. M. Nagatomo, “Oxaziridine-Mediated Enantioselective Aminohydroxylation of Styrenes,” J. Synth. Org. Chem., Jpn. 2013, 71, 944–945.
    DOI: 10.5059/yukigoseikyokaishi.71.944

Book Chapters

  1. 長友優典 “網羅的全合成戦略の探求　プリビレッジな構造の抽出と構築,”　 化学と工業 飛翔する若手研究者, 日本化学会, pp 584–585 (2023).

  2. M. Nagatomo, “Total Syntheses of Densely Oxygenated Natural Products by Radical-Based Decarbonylative Convergent Assembly,”　 New Tide of Natural Product Chemistry, Springer, Singapore, pp 259–273 (2023).
    DOI: 10.1007/978-981-99-1714-3_12

  3. Submitted by Y. Xue, A. Parsad, G. Dong, Checked by J. Han, M. Nagatomo, M. Inoue, “α-Arylation of Cyclopentanones by Palladium/Enamine Cooperative Catalysis,” Org. Synth. 2023, 100, 99–112.
    DOI: 10.15227/orgsyn.100.0099

  4. Submitted by M. Varghese, H. E. Caputo, R. Xiao, A. Balijepalli, A. Hamoud, M. W. Grinstaff, Checked by K. Oga, M. Nagatomo, M. Inoue, “Stereoselective [2+2] Cycloadditions: Synthesis of a Tri-O-Bn-D-Glucal-derived β-Lactam,” Org. Synth. 2021, 98, 491–508.
    DOI: 10.15227/orgsyn.098.0491

  5. Submitted by Y. Chen, Q. Chen, L. Tan, L. Chen, X. Wang, Checked by Y. Komori, M. Nagatomo, M. Inoue, “Preparation of 1H-Indazole-3-carbonitrile,” Org. Synth. 2020, 97, 314–326.
    DOI: 10.15227/orgsyn.097.0314

  6. Submitted by J. Klepp, W. Dillon, Y. Lin, P. Feng, B. W. Greatrex, Checked by Y. Imamura, M. Nagatomo, M. Inoue, “Preparation of (-)-Levoglucosenone from Cellulose Using Sulfuric Acid in Polyethylene Glycol,” Org. Synth. 2020, 97, 38–53.
    DOI: 10.15227/orgsyn.097.0038

  7. Submitted by Y. Kawashima, T. Furukawa, N. Chatani, M. Tobisu, Checked by T. Fukuda, M. Nagatomo, M. Inoue, “Nickel-Catalyzed Cross-Coupling of 2-Methoxynaphthalene with Methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate,” Org. Synth. 2019, 96, 36–52.
    DOI: 10.15227/orgsyn.096.0036

  8. 長友優典, 井上将行, “リアノダンジテルペンの統一的全合成,”　 天然有機化合物の全合成　独創的なものづくりの反応と戦略(CSJカレントレビュー 27) (日本化学会　編), 化学同人, pp 103–109 (2018).

Others

  1. 長友優典, 今村祐亮, 井上将行, “抗がん剤タキソールの全合成――ラジカル反応を活用した新しい合成戦略とその展開,” 化学 2023, 78 (7), 33–37.
    (Associated Link: Link)

  2. 長友優典、”高酸化度天然物の全合成戦略の開発,” 薬事日報 2018, 11995, 21.

  3. 井上将行、 長友優典、占部大介、”ラジカル反応を基盤とした高酸化度天然物の収束的合成戦略,” ファルマシア 2017, 53(9), 860–864.

  4. 長友優典, 井上将行, “リアノジン類の統一的全合成-多様性を志向した共通中間体の設計戦略,” 化学 2016, 71(4), 47–48.
    (Associated Link: Link)

  5. T. Hoshikawa, M. Nagatomo, M. Inoue, “Pentafluorophenyl Isocyanate,” e-EROS 2013, RN01621.
    DOI: 10.1002/047084289X.rn01621
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