Phosphono-δ-lactones are widely used as bioactive compounds, flame retardants, and polymer building blocks. Over the past years, new methods to access this heterocycle have been developed, some of them using innovative methodologies, like electrochemistry or photocatalysis. The current microreview covers selected methods over the past 5 years.
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Parsons, D. E.; Lee, S. H.; Sun, Y. J.; Velez, G.; Bassuk, A. G.; Smith, M.; Mahajan, V. B. Biomolecules 2021, 11, 339.
Uchiyama, A.; Mukai, M.; Fujiwara, Y.; Kobayashi, S.; Kawai, N.; Murofushi, H.; Inoue, M.; Enoki, S.; Tanaka, Y.; Niki, T.; Kobayashi, T.; Tigyi, G.; Murakami-Murofushi, K. Biochim. Biophys. Acta, Mol. Cell Biol. Lipids 2007, 1771, 103.
(a) Kaur, K.; Adediran, S. A.; Lan, M. J. K.; Pratt, R. F. Biochemistry 2003, 42, 1529. (b) Dutta, S.; Malla, R. K.; Bandyopadhyay, S.; Spilling, C. D.; Dupureur, C. M. Bioorg. Med. Chem. 2010, 18, 2265. (c) Point, V.; Malla, R. K.; Diomande, S.; Martin, B. P.; Delorme, V.; Carriere, F.; Canaan, S.; Rath, N. P.; Spilling, C. D.; Cavalier, J.-F. J. Med. Chem. 2012, 55, 10204.
Salmeia, K. A.; Gaan, S. Polym. Degrad. Stab. 2015, 113, 119.
Bauer, K. N.; Liu, L.; Andrienko, D.; Wagner, M.; Macdonald, E. K.; Shaver, M. P.; Wurm, F. R. Macromolecules 2018, 51, 1272.
Volle, J.-N.; Guillon, R.; Bancel, F.; Bekro, Y.-A.; Pirat, J.-L.; Virieux, D. In Advances in Heterocyclic Chemistry; Scriven, E.; Ramsden, C. A., Eds.; Elsevier: New York, 2016, vol. 118, p. 129.
Berton, J. K. E. T.; Heugebaert, T. S. A.; Virieux, D.; Stevens, C. V. Chem.–Eur. J. 2017, 23, 17413.
Xu, J. Chem. Heterocycl. Compd. 2020, 56, 979. [Khim. Geterotsikl. Soedin. 2020, 56, 979.]
Pérez-Saavedra, B.; Vázquez-Galiñanes, N.; Saá, C.; Fañanás-Mastral, M. ACS Catal. 2017, 7, 6104.
Bedalov, A.; Gatbonton, T.; Irvine, W. P.; Gottschling, D. E.; Simon, J. A. Proc. Natl. Acad. Sci. U. S. A. 2001, 98, 15113.
Wu, M.; Jiang, J.; Zhu, Z.; Wang, Q.; Kong, D. Synthesis 2018, 139.
(a) Ding, K.; Lu, Y.; Nikolovska-Coleska, Z.; Wang, G.; Qiu, S.; Shangary, S.; Gao, W.; Qin, D.; Stuckey, J.; Krajewski, K.; Roller, P. P.; Wang, S. J. Med. Chem. 2006, 49, 3432. (b) Kitahara, K.; Shimokawa, J.; Fukuyama, T. Chem. Sci. 2014, 5, 904. (c) Ma, Y.; Fan, C.; Jia, B.; Cheng, P.; Liu, J.; Ma, Y.; Qiao, K. Chirality 2017, 29, 737.
Huang, T.; Liu, L.; Wang, Q.; Wu, M.; Kong, D. Synthesis 2020, 1387.
Sheldon, R. A. Green Chem. 2017, 19, 18.
Zhang, L.; Zhang, Z.; Zhang, J.; Li, K.; Mo, F. Green Chem. 2018, 20, 3916.
Garrido-Castro, A. F.; Salaverri, N.; Maestro, M. C.; Alemán, J. Org. Lett. 2019, 21, 5295.
Bhanthumnavin, W.; Bentrude, W. G. J. Org. Chem. 2001, 66, 980.
Hernández-Guerra, D.; Kennedy, A. R.; León, E. I.; Martín, Á.; Pérez-Martín, I.; Rodríguez, M. S.; Suárez, E. J. Org. Chem. 2020, 85, 4861.
Qiao, M.-M.; Liu, Y.-Y.; Yao, S.; Ma, T.-C.; Tang, Z.-L.; Shi, D.-Q.; Xiao, W.-J. J. Org. Chem. 2019, 84, 6798.
Li, B.; Zhou, B.; Lu, H.; Ma, L.; Peng, A.-Y. Eur. J. Med. Chem. 2010, 45, 1955.
Xiao, Z.; Peng, A.-Y. Synthesis 2019, 3499.
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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(12), 1167–1169
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Ceradini, D., Shubin, K. New methods for the synthesis of phosphono-δ-lactones (microreview). Chem Heterocycl Comp 57, 1167–1169 (2021). https://doi.org/10.1007/s10593-021-03038-7
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DOI: https://doi.org/10.1007/s10593-021-03038-7