[1] P. Ertl, E. Altmann, J. M. McKenna, J. Med. Chem. 2020, 63, 8408-8418.
[2] R. D. Taylor, M. MacCoss, A. D. Lawson, J. Med. Chem. 2014, 57, 5845-5859.
[3] a) S. Knapp, A. T. Levorse, J. Org. Chem. 1988, 53, 4006- 4014; b) R. Göttlich, in Catalysis from A to Z, 2020.
[4] a) R. E. Gawley, in Organic Reactions, 2004, pp. 1-420; b) S. Xu, H. Arimoto, D. Uemura, Angew. Chem. Int. Ed. 2007, 46, 5746-5749.
[5] a) E. Nyfeler, P. Renaud, CHIMIA 2006, 60, 276-284; b) S. Lang, J. A. Murphy, Chem. Soc. Rev. 2006, 35, 146-156.
[6] M. Kinugasa, S. Hashimoto, J. Chem. Soc., Chem. Commun. 1972, 466-467.
[7] Base-mediated approaches and microwave-assisted approaches have been also reported. These approaches are also suffer from hash reaction conditions (high temperature and long time). See: a) J. Caruano, G. G. Muccioli, R. Robiette, Org. Biomol. Chem. 2016, 14, 10134–10156; b) T. D. Phi, H. Doan Thi Mai, V. H. Tran, B. N. Truong, T. A. Tran, V. L. Vu, V. M. Chau, V. C. Pham, Med. Chem. Commun. 2017, 8, 445–451 and references therein.
[8] a) M. Mader, P. Helquist, Tetrahedron Lett. 1988, 29, 3049- 3052; b) M. Arkhipova, S. Eichel, G. Maas, RSC Adv. 2014, 4, 56506-56517.
[9] a) A. Burkhart, H. Ritter, Beilstein J. Org. Chem. 2014, 10, 1951-1958; b) A. Bladé-Font, Tetrahedron Lett. 1980, 21, 2443-2446.
[10] R. M. Lanigan, P. Starkov, T. D. Sheppard, J. Org. Chem. 2013, 78, 4512-4523.
[11] K. Ishihara, S. Ohara, H. Yamamoto, J. Org. Chem. 1996, 61, 4196-4197.
[12] K. Steliou, A. Szczygielska-Nowosielska, A. Favre, M. A. Poupart, S. Hanessian, J. Am. Chem. Soc. 1980, 102, 7578-7579.
[13] Y. Yamamoto, T. Furuta, Chem. Lett. 1989, 18, 797-800.
[14] F. de Azambuja, T. N. Parac-Vogt, ACS Catal. 2019, 9, 10245-10252.
[15] V. Radha Rani, N. Srinivas, S. J. Kulkarni, K. V. Raghavan, J. Mol. Catal. A: Chem. 2002, 187, 237-246.
[16] a) R. De Wachter, L. Brans, S. Ballet, I. Van den Eynde, D. Feytens, A. Keresztes, G. Toth, Z. Urbanczyk-Lipkowska, D. Tourwé, Tetrahedron 2009, 65, 2266-2278; b) J. M. Andrés, N. de Elena, R. Pedrosa, A. Pérez-Encabo, Tetrahedron: Asymmetry 2001, 12, 1503-1509.
[17] a) G. Forcher, A. Silvanus, P. de Frémont, B. Jacques, M. S. M. Pearson-Long, F. Boeda, P. Bertus, J. Organomet. Chem. 2015, 797, 1-7; b) O. Srinivas, P. Larrieu, E. Duverger, M.-T. Bousser, M. Monsigny, J.-F. Fonteneau, F. Jotereau, A.-C. Roche, Bioconjugate Chem. 2007, 18, 1547-1554.
[18] a) W.-c. Chang, Y. Guo, C. Wang, S. E. Butch, A. C. Rosenzweig, A. K. Boal, C. Krebs, J. M. Bollinger, Science 2014, 343, 1140; b) C. R. Zwick, H. Renata, J. Org. Chem. 2018, 83, 7407-7415.
[19] Recent selected reviews for continuous-flow synthesis, see: a) S. Kobayashi, Chem. Asian J. 2016, 11, 425-436; b) J. Britton, C. L. Raston, Chem. Soc. Rev. 2017, 46, 1250- 1271; c) M. B. Plutschack, B. Pieber, K. Gilmore, P. H. Seeberger, Chem. Rev. 2017, 117, 11796-11893; d) F. Fanelli, G. Parisi, L. Degennaro, R. Luisi, Beilstein J. Org. Chem. 2017, 13, 520-542; e) C. A. Shukla, A. A. Kulkarni, Beilstein J. Org. Chem. 2017, 13, 960-987; f) R. Gérardy, N. Emmanuel, T. Toupy, V.-E. Kassin, N. N. Tshibalonza, M. Schmitz, J.-C. M. Monbaliu, Eur. J. Org. Chem. 2018, 2018, 2301-2351; g) B. T. Ramanjaneyulu, N. K. Vishwakarma, S. Vidyacharan, P. R. Adiyala, D.-P. Kim, Bull. Korean Chem. Soc. 2018, 39, 757-772; h) L. Rogers, K. F. Jensen, Green Chem. 2019, 21, 3481-3498; i) C. Mateos, M. J. Nieves-Remacha, J. A. Rincón, React. Chem. Eng. 2019, 4, 1536-1544; j) V. R. L. J. Bloemendal, M. A. C. H. Janssen, J. C. M. van Hest, F. P. J. T. Rutjes, React. Chem. Eng. 2020, 5, 1186-1197; k) D. L. Hughes, Org. Process Res. Dev. 2020, 24, 1850-1860; l) M. Baumann, T. S. Moody, M. Smyth, S. Wharry, Org. Process Res. Dev. 2020, 24, 1802-1813; m) M. Baumann, T. S. Moody, M. Smyth, S. Wharry, Eur. J. Org. Chem. 2020, 2020, 7398- 7406; n) M. Guidi, P. H. Seeberger, K. Gilmore, Chem. Soc. Rev. 2020, 49, 8910-8932.
[20] a) B. Gutmann, D. Cantillo, C. O. Kappe, Angew. Chem. Int. Ed. 2015, 54, 6688-6728; b) M. Movsisyan, E. I. P. Delbeke, J. K. E. T. Berton, C. Battilocchio, S. V. Ley, C. V. Stevens, Chem. Soc. Rev. 2016, 45, 4892-4928; c) N. Kockmann, P. Thenée, C. Fleischer-Trebes, G. Laudadio, T. Noël, React. Chem. Eng. 2017, 2, 258-280.
[21] N. G. Anderson, Org. Process Res. Dev. 2012, 16, 852-869.
[22] a) J.-i. Yoshida, Flash Chemistry - Fast Organic Synthesis in Micro Systems, WILEY-VCH, Weinheim, 2008; b) J.-i. Yoshida, A. Nagaki, T. Yamada, Chem. Eur. J. 2008, 14, 7450-7459; c) J.-i. Yoshida, Chem. Rec. 2010, 10, 332-341; d) J.-i. Yoshida, Y. Takahashi, A. Nagaki, Chem. Commun. 2013, 49, 9896-9904.
[23] a) M. Colella, A. Nagaki, R. Luisi, Chem. Eur. J. 2020, 26, 19-32; b) M. Power, E. Alcock, G. P. McGlacken, Org. Process Res. Dev. 2020, 24, 1814-1838.
[24] a) S. Fuse, N. Tanabe, T. Takahashi, Chem. Commun. 2011, 47, 12661-12663; b) S. Fuse, Y. Mifune, T. Takahashi, Angew. Chem. Int. Ed. 2014, 53, 851-855; c) S. Fuse, Y. Mifune, H. Nakamura, H. Tanaka, Nat. Commun. 2016, 7, 13491; d) Y. Mifune, H. Nakamura, S. Fuse, Org. Biomol. Chem. 2016, 14, 11244-11249; e) Y. Otake, H. Nakamura, S. Fuse, Angew. Chem. Int. Ed. 2018, 57, 11389-11393; f) Y. Otake, H. Nakamura, S. Fuse, Angew. Chem. Int. Ed. 2018, 57, 11389-11393; g) S. Fuse, K. Masuda, Y. Otake, H. Nakamura, Chem. Eur. J. 2019, 25, FULL PAPER 8 15091-15097; h) N. Sugisawa, Y. Otake, H. Nakamura, S. Fuse, Chem. Asian J. 2020, 15, 79-84; i) N. Sugisawa, H. Nakamura, S. Fuse, Chem. Commun. 2020, 56, 4527- 4530; j) Y. Otake, Y. Shibata, Y. Hayashi, K. Susumu, N. Hiroyuki, S. Fuse, Angew. Chem. Int. Ed. 2020, 59, 12925- 12930.
[25] S. Fuse, Y. Otake, H. Nakamura, Chem. Asian J. 2018, 13, 3818-3832.
[26] a) F. Albericio, J. M. Bofill, A. El-Faham, S. A. Kates, J. Org. Chem. 1998, 63, 9678-9683; b) A. El-Faham, F. Albericio, Chem. Rev. 2011, 111, 6557-6602; c) F. Albericio, A. ElFaham, Org. Process Res. Dev. 2018, 22, 760-772.
[27] Rapid mixing of organic-aqueous biphasic solution was required at the first mixer, therefore, the V-shaped mixer was used to avoid the undesired reaction. We previously reported better mixing of the V-shaped mixer compared with that of the T-shaped mixer. See ref. [24e].
[28] M. L. Bender, B. W. Turnquest, J. Am. Chem. Soc. 1957, 79, 1656-1662.
[29] H. K. Hall, J. Phys. Chem. 1956, 60, 63-70.
[30] H. K. Hall, J. Am. Chem. Soc. 1957, 79, 5441-5444.
[31] C. Faltin, E. M. Fleming, S. J. Connon, J. Org. Chem. 2004, 69, 6496-6499.
[32] F. Ravalico, S. L. James, J. S. Vyle, Green Chem. 2011, 13, 1778-1783.
[33] Amounts of NMM and triphosgene, concentrations, temperatures were optimized. For details, see Supporting Information.
[34] Amounts of NMI and triphosgene, and reaction times were optimized. For details, see Supporting Information.
[35] M. A. Dechantsreiter, E. Planker, B. Mathä, E. Lohof, G. Hölzemann, A. Jonczyk, S. L. Goodman, H. Kessler, J. Med. Chem. 1999, 42, 3033-3040.
[36] Reviews for continuous-flow peptide synthesis, see: a) S. Ramesh, P. Cherkupally, B. G. de la Torre, T. Govender, H. G. Kruger, F. Albericio, Amino Acids 2014, 46, 2091-2104; b) N. Ahmed, Chem. Biol. Drug. Des. 2018, 91, 647-650; c) S. Fuse, Y. Otake, H. Nakamura, Chem. Asian J. 2018, 13, 3818-3832; d) C. P. Gordon, Org. Biomol. Chem. 2018, 16, 180-196; Continuous-flow cyclic peptide synthesis, see: e) D. Lücke, T. Dalton, S. V. Ley, Z. E. Wilson, Chem. Eur. J. 2016, 22, 4206-4217; f) N. Ollivier, T. Toupy, R. C. Hartkoorn, R. Desmet, J.-C. M. Monbaliu, O. Melnyk, Nat. Commun. 2018, 9, 2847; g) T. Ohara, M. Kaneda, T. Saito, N. Fujii, H. Ohno, S. Oishi, Bioorg. Med. Chem. Lett. 2018, 28, 1283-1286.
[37] A. I. Fernández-Llamazares, J. Adan, F. Mitjans, J. Spengler, F. Albericio, Bioconjugate Chem. 2014, 25, 11- 17; In 2010, Albericio and coworkers also reported macrolactamization for protected cilengitide (88% yield) using PyBOP or PyAOP and HOAt in DMF/DCM under high dilution (0.05 mM) conditions (our conditions: 3.3 mM). Detailed reaction conditions (a coupling agent, amounts, temperature, time) are not described: T. Cupido, J. Spengler, J. Ruiz-Rodriguez, J. Adan, F. Mitjans, J. Piulats, F. Albericio, Angew. Chem. Int. Ed. 2010, 49, 2732-2737.
[38] J. O. Goldsmith, S. Lee, I. Zambidis, L. C. Kuo, J. Biol. Chem. 1991, 266, 18626-18634.
[39] M. Abe, T. Akiyama, H. Nakamura, F. Kojima, S. Harada, Y. Muraoka, J. Nat. Prod. 2004, 67, 999-1004.
[40] M. Abe, T. Akiyama, Y. Umezawa, K. Yamamoto, M. Nagai, H. Yamazaki, Y.-i. Ichikawa, Y. Muraoka, Bioorg. Med. Chem. 2005, 13, 785-797.
[41] L. U. Nordstrøm, H. Vogt, R. Madsen, J. Am. Chem. Soc. 2008, 130, 17672-17673.
[42] a) G. M. Wall, J. K. Baker, J. Med. Chem. 1989, 32, 1340- 1348; b) S. J. P. Yoon-Miller, S. M. Opalka, E. T. Pelkey, Tetrahedron Lett. 2007, 48, 827-830.
[43] X. Peng, H.-H. Wang, F. Cao, H.-H. Zhang, Y.-M. Lu, X.-L. Hu, W. Tan, Z. Wang, Org. Chem. Front. 2019, 6, 1837- 1841.
[44] W. R. Ewing, M. R. Becker, V. E. Manetta, R. S. Davis, H. W. Pauls, H. Mason, Y. M. Choi-Sledeski, D. Green, D. Cha, A. P. Spada, D. L. Cheney, J. S. Mason, S. Maignan, J.-P. Guilloteau, K. Brown, D. Colussi, R. Bentley, J. Bostwick, C. J. Kasiewski, S. R. Morgan, R. J. Leadley, C. T. Dunwiddie, M. H. Perrone, V. Chu, J. Med. Chem. 1999, 42, 3557-3571.
[45] S. C. Ghosh, S. Muthaiah, Y. Zhang, X. Xu, S. H. Hong, Adv. Synth. Catal. 2009, 351, 2643-2649.
[46] K. Y. Koltunov, G. K. S. Prakash, G. Rasul, G. A. Olah, J. Org. Chem. 2002, 67, 8943-8951.
[47] C. F. Hammer, S. Chandrasegaran, J. Am. Chem. Soc. 1984, 106, 1543-1552.
[48] a) M. Sayes, A. B. Charette, Green Chem. 2017, 19, 5060- 5064; b) K. L. Yu, G. Rajakumar, L. K. Srivastava, R. K. Mishra, R. L. Johnson, J. Med. Chem. 1988, 31, 1430-1436.
[49] J. Xu, Y. Gao, Z. Li, J. Liu, T. Guo, L. Zhang, H. Wang, Z. Zhang, K. Guo, Eur. J. Org. Chem. 2020, 2020, 311-315.
論文の公開元へ
