10.1002/adsc.202000886
Advanced Synthesis & Catalysis
T. Lindhorst, Y. Queneau), Royal Society of Chemistry,
2017, pp 313-343.
tuberculosis, cancers, viral infections, diabetes and
cystic fibrosis. For a set of publications see also a) A.
Esposito, D. D’Alonzo, M. De Fenza, E. De Gregorio,
A. Tamanini, G. Lippi, M. C. Dechecchi, A. Guaragna,
Int. J. Mol. Sci. 2020, 21, 3353; b) S. Rajasekharan, R.
M. Bonotto, Y. Kazungu, N. L. Alves, M. Poggianella,
P. M. Orellana, N. Skoko, S. Polez, A. Marcello,
bioRxiv 2020, in press; c) F. Hossain, P. R. Andreana,
Pharmaceuticals 2019, 12, 84; d) J. L. Miller, B. E.
Tyrrell, N. Zitzmann Mechanisms of Antiviral Activity
of Iminosugars Against Dengue Virus. In Dengue and
Zika: Control and Antiviral Treatment Strategies, Vol.
1062 (Eds.: R. Rolf Hilgenfeld, S. G. Vasudevan),
Springer: Berlin/Heidelberg, Germany, 2018, pp. 277-
301; e) A. Wadood, M. Ghufran, A. Khan, S. S. Azam,
M. Jelani, R. Uddin, Int. J. Biol. Macromol. 2018, 111,
82-91; f) C. Cocaud, A. Maujoin, R. B. Zheng, T. L.
Lowary, N. Rodrigues, N. Percina, A. Chartier, F.
Buron, S. Routier, C. Nicolas, O. R. Martin, Eur. J.
Org. Chem. 2017, 6192-6201; g) N. F. Bras, N. M.
Cerqueira, M. J. Ramos, P. A. Fernandes, Expert Opin.
Ther. Pat. 2014, 24, 857-874.
[15] a) H. Hensienne, D. Hazelard, P. Compain,
ARKIVOC 2019, 4-43; b) C. Dehoux-Baudoin, Y.
Génisson, Eur. J. Org. Chem. 2019, 4765-4777.
[16] a) A. Kato, I. Nakagome, K. Sato, A. Yamamoto, I.
Adachi, R. J. Nash, G. W. J. Fleet, Y. Natori, Y.
Watanabe, T. Imahori, Y. Yoshimura, H. Takahata, S.
Hirono, Org. Biomol. Chem. 2016, 14, 1039-1048. b) Y.
Natori, T. Imahori, Y. Yoshimura, J. Synth. Org. Chem.,
Jpn. 2016, 74, 335-349; c) Y. Natori, T. Sakuma, Y.
Yoshimura, K. Kinami, Y. Hirokami, K. Sato, I.
Adachi, A. Kato, H. Takahata, Bioorg. Med. Chem. Lett.
2014, 24, 3298-3301; d) A. Kato, E. Hayashi, S.
Miyauchi, I. Adachi, T. Imahori, Y. Natori, Y.
Yoshimura, R. J. Nash, H. Shimaoka, I. Nakagome, J.
Kosegi, S. Hirono, H. Takahata, J. Med. Chem. 2012,
55, 10347-10362; e) Y. Natori, S. Kikuchi, Y.
Yoshimura, A. Kato, I. Adachi, H. Takahata,
Heterocycles 2012, 86, 1401-1417; f) Y. Natori, T.
Imahori, K. Murakami, Y. Yoshimura, S. Nakagawa, A.
Kato, I. Adachi, H. Takahata, Bioorg. Med. Chem. Lett.
2011, 21, 738-741.
[22] C. Cocaud, C. Nicolas, A. Bayle, T. Poisson, X.
Pannecoucke, O. R. Martin, Eur. J. Org. Chem. 2015,
4330-4334.
[17] A seminal work by Le Grognec et al., concerning
possible routes to enantiopure 2-deoxy- and 2,3-
dideoxy- iminosugar-C-glycosides has been reported.
The key synthetic steps involve a diastereoselective tin-
lithium exchange and an electrophilic trapping
sequence combined with ring-closing metathesis of
[23] K. W. Kells, J. M. Chong, Org. Lett. 2003, 5, 4215-
4218.
[24] N. Plobeck, D. Powell, Tetrahedron: Asymmetry
2002, 13, 303-310.
stannylated
oxazolidinones,
disubstituted
[25] a) N. T. Anh, O. Eisenstein, Nouv. J. Chim. 1977, 1,
61-70; b) N. T. Anh, O. Eisenstein, J.-M. Lefour, M.-E.
Dau, J. Am. Chem. Soc. 1973, 95, 6146-6147.
dehydropiperidines and dehydroazepanes. See: a) A.
Lumbroso, I. Beaudet, J.-P. Quintard, C. Fraisse, N.
Galland, L. Toupet, E. Le Grognec, Adv. Synth. Catal.
2019, 361, 3777-3486; b) A. Lumbroso, I. Beaudet, L.
Toupet, E. Le Grognec, J.-P. Quintard, Org. Lett. 2013,
15, 160-163.
[26] a) C. Cocaud, R. B. Zheng, T. L. Lowary, T. Poisson,
X. Pannecoucke, C. Nicolas, O. R. Martin, Carbohydr.
Res. 2018, 461, 45-50.
[18] a) D. Antermite, J. A. Bull, Synthesis 2019, 51, A-
AH; b) L. Gonnard, A. Guérinot, J. Cossy, Tetrahedron
2019, 75, 145-163; c) E. A. Mitchell, A. Peschiulli, N.
Lefevre, L. Meerpoel, B. U. W. Maes, Chem. Eur. J.
2012, 18, 10092-10142.
[27] M. T. Robak, M. A. Herbage, J. A. Ellman, Chem.
Rev. 2010, 110, 3600-3740.
[28] K. W. Kells, J. M. Chong, J. Am. Chem. Soc. 2004,
126, 15666-15667.
[29] P. Sun, S. M. Weinreb, J. Org. Chem. 1997, 62,
[19] A. Mordini, M. Valacchi, F. Epiroti, G. Reginato, S.
8604-8608.
Cicchi, A. Goti, Synlett 2011, 235-240.
[30] S. Hanessian, X. Wang, Synthesis 2009, 2803-2808.
[20] a) F. Zhu, S. O’Neill, J. Rodriguez, M. A. Walczak,
Chem. Eur. J. 2019, 25, 3147-3155; b) F. Zhu, J.
Rodriguez, S. O’Neill, M. A. Walczak, ACS Cent. Sci.
2018, 4, 1652-1662; c) D. Yi, F. Zhu, M. A. Walczak,
Org. Lett. 2018, 20, 4627-4631; d) D. Yi, F. Zhu, M. A.
Walczak, Org. Lett. 2018, 20, 1936-1940; e) F. Zhu, J.
Rodriguez, T. Yang, I. Kevlishvili, E. Miller, D. Yi, S.
O’Neill, M. J. Rourke, P. Liu, M. A. Walczak, J. Am.
Chem. Soc. 2017, 139, 17908-17922; f) F. Zhu, M. J.
Rourke, T. Yang, J. Rodriguez, M. A. Walczak, J. Am.
Chem. Soc. 2016, 138, 12049-12052.
[31] a) S. Toumieux, P. Compain, O. R. Martin, J. Org.
Chem. 2008, 73, 2155-2162; b) S. Toumieux, P.
Compain, O. R. Martin, M. Selkti, Org. Lett. 2006, 8,
4493-4496.
[32] P. Uhlmann, D. Nanz, E. Bozꢁ, A. Vasella, Helv.
Chim. Acta 1994, 77, 1430-1440.
[33] C. Cordovilla, C. Bartolomé, J. M. Martínez-Ilarduya,
P. Espinet, ACS Catal. 2015, 5, 3040-3053 and
references cited therein.
[21] Sulfinylglycosylamines 10a‒e are precursors of
hydrolytically stable iminosugar glycomimetics of type
25a‒g with D-Galf-like, L-xylof, L-lyxof, D-Gulop-like
and D-Glcp-like configuration. Compounds 25a‒g are
thus promising chemotherapeutics for the treatment of
[34] D. Azarian, S. S. Dua, C. Eaborn, D. R. M. Walton, J.
Organomet. Chem. 1976, 117, C55−C57.
[35] a) M. Kosugi, Y. Shimizu, T. Migita, Chem. Lett.
1977, 6, 1423-1424; b) M. Kosugi, K. Sasazawa, Y.
13
This article is protected by copyright. All rights reserved.