Diversification of Simple Arenes into Complex (Amino)cyclitols.
aminocyclitols
arenes
dearomatization
diversification
drug discovery
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
19 Oct 2023
19 Oct 2023
Historique:
received:
10
10
2023
pubmed:
19
10
2023
medline:
19
10
2023
entrez:
19
10
2023
Statut:
aheadofprint
Résumé
Highly oxygenated cyclohexanes, including (amino)cyclitols, are featured in natural products possessing a notable range of biological activities. As such, these building blocks are valuable tools for medicinal chemistry. While de novo synthetic strategies have provided access to select compounds, challenges including stereochemical density and complexity have hindered the development of a general approach to (amino)cyclitol structures. This work reports the use of arenophile chemistry to access dearomatized intermediates which are amenable to diverse downstream transformations. Practical guidelines were developed for the synthesis of natural and non-natural (amino)cyclitols from simple arenes through a series of strategic functionalization events.
Identifiants
pubmed: 37856371
doi: 10.1002/chem.202303262
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202303262Subventions
Organisme : HORIZON EUROPE European Research Council
ID : 804583
Informations de copyright
© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
Références
A. W. Dombrowski, N. J. Gesmundo, A. L. Aguirre, K. A. Sarris, J. M. Young, A. R. Bogdan, M. C. Martin, S. Gedeon, Y. Wang, ACS Med. Chem. Lett. 2020, 11, 597-604.
W. R. Galloway, D. R. Spring, Expert Opin. Drug Discovery 2009, 4, 467-472;
F. Lovering, J. Bikker, C. Humblet, J. Med. Chem. 2009, 52, 6752-6756.
B. J. Huffman, R. A. Shenvi, J. Am. Chem. Soc. 2019, 141, 3332-3346.
R. J. Young, S. L. Flitsch, M. Grigalunas, P. D. Leeson, R. J. Quinn, N. J. Turner, H. Waldmann, JACS Au 2022, 2, 2400-2416.
M. Grigalunas, S. Brakmann, H. Waldmann, J. Am. Chem. Soc. 2022, 144, 3314-3329.
J. Shearer, J. L. Castro, A. D. G. Lawson, M. MacCoss, R. D. Taylor, J. Med. Chem. 2022, 65, 8699-8712.
L. Diaz, A. Delgado, Curr. Med. Chem. 2010, 17, 2393-2418.
O. Arjona, A. M. Gómez, J. C. López, J. Plumet, Chem. Rev. 2007, 107, 1919-2036;
L. S. Jeong, J. A. Lee, Antiviral Chem. Chemother. 2004, 15, 235-250;
S. Horii, H. Fukase, T. Matsuo, Y. Kameda, N. Asano, K. Matsui, J. Med. Chem. 1986, 29, 1038-1046;
S. Yaginuma, N. Muto, M. Tsujino, Y. Sudate, M. Hayashi, M. Otani, J. Antibiot. 1981, 34, 359-366.
A. S. Dabhi, N. R. Bhatt, M. J. Shah, J. Clin. Diagn. Res. 2013, 7, 3023-3027;
L. Siracusa, E. Napoli, G. Ruberto, Molecules 2022, 27, 1525.
G. R. Pettit, V. Gaddamidi, G. M. Cragg, J. Nat. Prod. 1984, 47, 1018-1020.
B. Becker, M. A. Cooper, ACS Chem. Biol. 2013, 8, 105-115.
For recent overview, see:
A. Delgado, Eur. J. Org. Chem. 2008, 23, 3893-3906;
E. Salamci, Tetrahedron Lett. 2020, 15, 151728.
L. Castellanos, J. Cléophax, C. Colas, S. D. Gero, J. Leboul, D. Mercier, A. Olesker, A. Rolland, B. Quiclet-Sire, A.-M. Sepulchre, Carbohydr. Res. 1980, 82, 283-301;
S. M. Jachak, N. P. Karche, D. D. Dhavale, Tetrahedron Lett. 2001, 42, 4925-4928.
S. Harada, K. Li, R. Kino, T. Takeda, C. H. Wu, S. Hiraoka, A. Nishida, Chem. Pharm. Bull. 2016, 64, 1474-1483;
C. Alegret, J. Benet-Buchholz, A. Riera, Org. Lett. 2006, 8, 3069-3072;
C. Chakraborty, V. P. Vyavahare, D. D. Dhavale, Tetrahedron 2007, 63, 11984-11990.
G. J. Merten, C. Neis, S. Stucky, V. Huch, E. Rentschler, H. Natter, R. Hempelmann, K. Stöwe, K. Hegetschweiler, Eur. J. Inorg. Chem. 2012, 1, 31-35.
For arenophile-mediated dearomatization strategies, see:
M. Okumura, D. Sarlah, Synlett 2018, 29, 845-855;
M. Okumura, D. Sarlah, Chimia 2020, 74, 577-577;
M. Okumura, D. Sarlah, Eur. J. Org. Chem. 2020, 10, 1259-1273.
For applications of dearomative chemistry in organic synthesis, see:
S. P. Roche, J. A. Porco, Angew. Chem. Int. Ed. 2011, 50, 4068-4093;
C. J. Huck, Y. D. Boyko, D. Sarlah, Nat. Prod. Rep. 2022, 39, 2231-2291.
M. Okumura, S. M. Nakamata Huynh, J. Pospech, D. Sarlah, Angew. Chem. Int. Ed. 2016, 55, 15910-15914.
E. H. Southgate, J. Pospech, J. Fu, D. R. Holycross, D. Sarlah, Nat. Chem. 2016, 8(10), 922-928.
V. VanRheenen, R. C. Kelly, D. Y. Cha, Tetrahedron Lett. 1976, 17, 1973-1976.
For selected examples, see:
T. Danjo, H. Yamada, T. Nakajima, WO Patent 2018235926 (2018);
R. Graceffa, M. Kaller, D. La, P. Lopez, V. F. Patel, W. Zhong, US Patent 20100120774 (2010);
K. D. Janda, T. J. Dickerson, WO Patent 2009120954 (2009).
L. F. Tietze, G. Kettschau in Stereoselective Heterocyclic Synthesis I (Ed.: P. Metz), Springer, Berlin, Heidelberg, 1997, pp. 1-120.
B. S. Bodnar, M. J. Miller, Angew. Chem. Int. Ed. 2011, 50, 5630-5647.
C. Cesario, L. P. Tardibono, M. J. Miller, J. Org. Chem. 2009, 74, 448-451.
Y. Sutbeyaz, H. Secen, M. Balci, J. Chem. Soc. Chem. Commun. 1988, 19, 1330-1331.
Deposition Number 2243206 (for 47) contains the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service.
Z. Siddiqi, W. C. Wertjes, D. Sarlah, J. Am. Chem. Soc. 2020, 142, 10125-10131.
D. D. Schmidt, W. Frommer, B. Junge, L. Miiller, W. Wingender, E. Truscheit, D. Schafer, Naturwissenschaften 1977, 64, 535;
S. Horii, Y. Kameda, K. Kawahara, J. Antibiot. 1972, 25, 48-53.
X. Chen, Y. Fan, Y. Zheng, Y. Shen, Chem. Rev. 2003, 103, 1955-1978.
W. H. B. Sauer, M. K. Schwarz, J. Chem. Inf. Comput. Sci. 2003, 43, 987-1003.
C. N. Ungarean, P. Galer, Y. Zang, K. S. Lee, J. M. Nagai, S. Lee, P. Liu, D. Sarlah, Nat. Synth. 2022, 1, 542-547.
V. L. Paddock, R. J. Phipps, A. Conde-Angulo, A. Blanco-Martin, C. Girò-Manas, L. J. Martin, A. J. P. White, A. C. Spivey, J. Org. Chem. 2011, 76, 1483-1486.
R. Campagne, F. Schäkel, R. Guillot, V. Alezra, C. Kouklovsky, Org. Lett. 2018, 20(7), 1884-1887.
W. Ding, J.-P. Yu, X.-X. Shi, L.-D. Nie, N. Quan, F.-L. Li, Tetrahedron: Asymmetry 2015, 26(18-19), 1037-1042.
L. Ji, D. Zhang, Q. Zhao, S. Hu, C. Qian, X.-Z. Chen, Tetrahedron 2013, 69(34), 7031-7037.
D. Mendez, A. Gaulton, A. P. Bento, J. Chambers, M. De Veij, E. Félix, M. P. Magariños, J. F. Mosquera, P. Mutowo, M. Nowotka, M. Gordillo-Marañón, F. Hunter, L. Junco, G. Mugumbate, M. Rodriguez-Lopez, F. Atkinson, N. Bosc, C. J. Radoux, A. Segura-Cabrera, A. R. Leach, Nucleic Acids Res. 2018, 47, D930-D940.
RDKit: Open-source cheminformatics. http://www.rdkit.org.
S. Wang, J. Witek, G. A. Landrum, S. Riniker, J. Chem. Inf. Model. 2020, 60, 2044-2058.
T. A. Halgren, J. Comput. Chem. 1996, 17, 490-519.
J. D. Hunter, Comput. Sci. Eng. 2007, 9, 90-95.
M. Waskom, J. Open Source Softw. 2021, 6, 3021.
Y.-K. Chang, B.-Y. Lee, D. J. Kim, G. S. Lee, H. B. Jeon, K. S. Kim, J. Org. Chem. 2005, 70(8), 3299-3302.
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. Puschmann, J. Appl. Crystallogr. 2009, 42, 339-341.
G. M. Sheldrick, Acta Crystallogr. 2015, A71, 3-8.
G. M. Sheldrick, Acta Crystallogr. 2008, A64, 112-122.