Abstract
Organic chemistry developed a series of synthetic strategies toward spiro-annulated carbohydrates as potential pharmaceutical drugs or developed new organic synthetic methodologies. The present chapter gives a general overview of the spiro-annulation of carbohydrates at the anomeric position. The main synthetic strategies can be summarized in five paths. Intramolecular cyclizations can be performed through two short tethers with their reactive ends generating the spirocycle or through a single tether reacting at the anomeric position for cyclization. The three other strategies rely on intermolecular reactions with a portion of the spirocycle only in the external substrate or also on the carbohydrate. Radical-mediated cyclization and cycloaddition reactions are the main strategies toward spiro-annulated carbohydrates. A special attention is paid to discussion of the stereocontrol of the anomeric configuration and also to yields in industrial syntheses or biological activities of the molecules. A specific attention is devoted to tofogliflozin and glycogen phosphorylase inhibitors both used as antihyperglycemic drugs and drug candidates, respectively.
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References
Vidal S (ed) (2019) Protecting groups: strategies and applications in carbohydrate chemistry. Wiley-VCH, Weinheim
Demchenko AV (ed) (2008) Handbook of chemical glycosylation: advances in stereoselectivity and therapeutic relevance. Wiley-VCH, Weinheim
Zulueta MML, Hung S-C (eds) (2016) Glycochemical synthesis: strategies and applications. Wiley-VCH, Weinheim
Chen G-R, Fei Zhong B, Huang X-T, Xie Y-Y, Xu J-L, Gola J, Steng M, Praly J-P (2001). Eur J Org Chem:2939–2946
Lambu MR, Hussain A, Sharma DK, Yousuf SK, Singh B, Tripathi AK, Mukherjee D (2014). RSC Adv 4:11023–11028
John Pal AP, Gupta P, Suman Reddy Y, Vankar YD (2010). Eur J Org Chem:6957–6966
Haudrechy A, Sinaÿ P (1992). Carbohydr Res 216:375–379
Yamanoi T, Oda Y, Muraishi H, Matsuda S (2008). Molecules 13:1840
Dondoni A, Marra A (2009). Tetrahedron Lett 50:3593–3596
Lin H-C, Chen Y-B, Lin Z-P, Wong FF, Lin C-H, Lin S-K (2010). Tetrahedron 66:5229–5234
Chen Y-B, Liu S-H, Hsieh M-T, Chang C-S, Lin C-H, Chen C-Y, Chen P-Y, Lin H-C (2016). J Org Chem 81:3007–3016
John Pal AP, Vankar YD (2010). Tetrahedron Lett 51:2519–2524
John Pal AP, Kadigachalam P, Mallick A, Doddi VR, Vankar YD (2011). Org Biomol Chem 9:809–819
Martín A, Salazar J, Suárez E (1995). Tetrahedron Lett 36:4489–4492
Betancor C, Dorta RL, Freire R, Prangé T, Suárez E (2000). J Org Chem 65:8822–8825
Martín A, Quintanal LM, Suárez E (2007). Tetrahedron Lett 48:5507–5511
Martín A, Pérez-Martín I, Suárez E (2009). Tetrahedron 65:6147–6155
Martín A, Pérez-Martín I, Suárez E (2005). Org Lett 7:2027–2030
Probst N, Grelier G, Ghermani N, Gandon V, Alami M, Messaoudi S (2017). Org Lett 19:5038–5041
Pezzotta J, Urban D, Guillot R, Doisneau G, Beau J-M (2014). Synlett 25:375–380
Briner K, Vasella A (1989). Helv Chim Acta 72:1371–1382
Blüchel C, Linden A, Vasella A (2001). Helv Chim Acta 84:3495–3502
Mangholz SE, Vasella A (1991). Helv Chim Acta 74:2100–2111
Vasella A, Waldraff CAA (1991). Helv Chim Acta 74:585–593
Somsák L, Praly J-P, Descotes G (1992). Synlett:119–120
Praly JP, El Kharraf Z, Descotes G (1990). Tetrahedron Lett 31:4441–4442
Blüchel C, Ramana CV, Vasella A (2003). Helv Chim Acta 86:2998–3036
Brand C, Rauch G, Zanoni M, Dittrich B, Werz DB (2009). J Org Chem 74:8779–8786
Vasella A, Witzig C, Waldraff C, Uhlmann P, Briner K, Bernet B, Panza L, Husi R (1993). Helv Chim Acta 76:2847–2875
Vasella A, Dhar P, Witzig C (1993). Helv Chim Acta 76:1767–1778
Lay L, Nicotra F, Panza L, Russo G (1995). Synlett:167–168
Schweizer F, Inazu T (2001). Org Lett 3:4115–4118
Zhang K, Schweizer F (2005). Synlett:3111–3115
Zhang K, Wang J, Sun Z, Nguyen D-H, Schweizer F (2007). Synlett:0239–0242
Zhang K, Mondal D, Zhanel GG, Schweizer F (2008). Carbohydr Res 343:1644–1652
Zhang K, Schweizer F (2009). Carbohydr Res 344:576–585
Praly JP, Brard L, Descotes G (1988). Tetrahedron Lett 29:2651–2654
Praly J-P, Kharraf ZE, Corringer P-J, Brard L, Descotes G (1990). Tetrahedron 46:65–75
Buchanan JG, Clelland APW, Wightman RH, Johnson T, Rennie RAC (1992). Carbohydr Res 237:295–301
Baddeley KL, Cao Q, Muldoon MJ, Cook MJ (2015). Chem Eur J 21:7726–7730
Zhang D, Ye D, Feng E, Wang J, Shi J, Jiang H, Liu H (2010). J Org Chem 75:3552–3557
McDonald FE, Zhu HYH, Holmquist CR (1995). J Am Chem Soc 117:6605–6606
Yamamoto Y, Yamashita K, Hotta T, Hashimoto T, Kikuchi M, Nishiyama H (2007). Chem Asian J 2:1388–1399
Bartolozzi A, Capozzi G, Falciani C, Menichetti S, Nativi C, Bacialli AP (1999). J Org Chem 64:6490–6494
Wrodnigg TM, Kartusch C, Illaszewicz C (2008). Carbohydr Res 343:2057–2066
Gallas K, Pototschnig G, Adanitsch F, Stütz AE, Wrodnigg TM (2012). Beilstein J Org Chem 8:1619–1629
Denmark SE, Regens CS, Kobayashi T (2007). J Am Chem Soc 129:2774–2776
Denmark SE, Kobayashi T, Regens CS (2010). Tetrahedron 66:4745–4759
Song KS, Lee SH, Kim MJ, Seo HJ, Lee J, Lee SH, Jung ME, Son EJ, Lee M, Kim J, Lee J (2011). ACS Med Chem Lett 2:182–187
Harada N, Inagaki N (2012). J Diabetes Investig 3:352–353
Madaan T, Akhtar M, Najmi AK (2016). Eur J Pharm Sci 93:244–252
Washburn WN (2012) SGLT2 inhibitors in development. In: Jones RM (ed) New therapeutic strategies for type 2 diabetes: small molecule approaches. The Royal Society of Chemistry, Cambridge, pp 29–87
Bokor É, Kun S, Goyard D, Tóth M, Praly JP, Vidal S, Somsák L (2017). Chem Rev 117:1687–1764
Aguillón AR, Mascarello A, Segretti ND, de Azevedo HFZ, Guimaraes CRW, Miranda LSM, de Souza ROMA (2018). Org Proc Res Dev 22:467–488
Poole RM, Prossler JE (2014). Drugs 74:939–944
Murakata M, Ikeda T, Kimura N, Kawase A, Nagase M, Yamamoto K, Takata N, Yoshizaki S, Takano K (2009) Crystal of spiroketal derivative, and process for production thereof. WO2009154276
Kobayashi T, Sato T, Nishimoto M (2005) Spiroketal derivative and use thereof as diabetic medicine. US2009030006
Kobayashi T, Sato T, Nishimoto M (2006) Preparation of 1,1-anhydro-1-C-[2-(hydroxyalkyl)aryl]-β-D-glucopyranose compounds as SGLT2 inhibitors. WO2006080421A1
Ohtake Y, Emura T, Nishimoto M, Takano K, Yamamoto K, Tsuchiya S, Yeu SY, Kito Y, Kimura N, Takeda S, Tsukazaki M, Murakata M, Sato T (2016). J Org Chem 81:2148–2153
Yang X-D, Pan Z-X, Li D-J, Wang G, Liu M, Wu R-G, Wu Y-H, Gao Y-C (2016). Org Process Res Dev 20:1821–1827
Ohtake Y, Sato T, Kobayashi T, Nishimoto M, Taka N, Takano K, Yamamoto K, Ohmori M, Yamaguchi M, Takami K, Yeu SY, Ahn KH, Matsuoka H, Morikawa K, Suzuki M, Hagita H, Ozawa K, Yamaguchi K, Kato M, Ikeda S (2012). J Med Chem 55:7828–7840
Ross SA, Gulve EA, Wang M (2004). Chem Rev 104:1255–1282
Morral N (2003). Trends Endocrinol Metab 14:169–175
Baker DJ, Greenhaff PL, Timmons JA (2006). Expert Opin Ther Pat 16:459–466
Khan M (2007). Top Heterocycl Chem 9:33–52
Somsák L, Czifrák K, Tóth M, Bokor E, Chrysina ED, Alexacou KM, Hayes JM, Tiraidis C, Lazoura E, Leonidas DD, Zographos SE, Oikonomakos NG (2008). Curr Med Chem 15:2933–2983
Praly J-P, Vidal S (2010). Mini-Rev Med Chem 10:1102–1126
Henke BR (2012) Inhibition of glycogen phosphorylase as a strategy for the treatment of type 2 diabetes. In: Jones RM (ed) New therapeutic strategies for type 2 diabetes: small molecule approaches. The Royal Society of Chemistry, Cambridge, pp 324–365
Gaboriaud-Kolar N, Skaltsounis A-L (2013). Expert Opin Ther Pat 23:1017–1032
Donnier-Maréchal M, Vidal S (2016). Expert Opin Ther Pat 26:199–212
Somsák L, Nagy V, Hadady Z, Docsa T, Gergely P (2003). Curr Pharm Des 9:1177–1189
Somsák L (2011). C R Chim 14:211–223
Praly J-P, Boyé S, Joseph B, Rollin P (1993). Tetrahedron Lett 34:3419–3420
Elek R, Kiss L, Praly J-P, Somsák L (2005). Carbohydr Res 340:1397–1402
Somsák L, Nagy V, Vidal S, Czifrák K, Berzsényi E, Praly J-P (2008). Bioorg Med Chem Lett 18:5680–5683
Nagy V, Benltifa M, Vidal S, Berzsényi E, Teilhet C, Czifrák K, Batta G, Docsa T, Gergely P, Somsák L, Praly J-P (2009). Bioorg Med Chem 17:5696–5707
RajanBabu TV, Reddy GS (1986). J Org Chem 51:5458–5461
Enderlin G, Taillefumier C, Didierjean C, Chapleur Y (2005). Tetrahedron Asymmetry 16:2459–2474
Benltifa M, Vidal S, Gueyrard D, Goekjian PG, Msaddek M, Praly J-P (2006). Tetrahedron Lett 47:6143–6147
Zhang P-Z, Li X-L, Chen H, Li Y-N, Wang R (2007). Tetrahedron Lett 48:7813–7816
Benltifa M, Hayes JM, Vidal S, Gueyrard D, Goekjian PG, Praly JP, Kizilis G, Tiraidis C, Alexacou KM, Chrysina ED, Zographos SE, Leonidas DD, Archontis G, Oikonomakos NG (2009). Bioorg Med Chem 17:7368–7380
Goyard D, Kónya B, Chajistamatiou AS, Chrysina ED, Leroy J, Balzarin S, Tournier M, Tousch D, Petit P, Duret C, Maurel P, Somsák L, Docsa T, Gergely P, Praly J-P, Azay-Milhau J, Vidal S (2016). Eur J Med Chem 108:444–454
Tite T, Tomas L, Docsa T, Gergely P, Kovensky J, Gueyrard D, Wadouachi A (2012). Tetrahedron Lett 53:959–961
Benltifa M, Kiss MD, Garcia-Moreno MI, Mellet CO, Gueyrard D, Wadouachi A (2009). Tetrahedron Asymmetry 20:1817–1823
Toumieux S, Compain P, Martin OR (2005). Tetrahedron Lett 46:4731–4735
Somsák L, Kovács L, Gyóllai V, Ősz E (1999). Chem Commun 7:591–592
Páhi A, Czifrák K, Kövér KE, Somsák L (2015). Carbohydr Res 403:192–201
Somsák L, Kovács L, Tóth M, Ősz E, Szilágyi L, Györgydeák Z, Dinya Z, Docsa T, Tóth B, Gergely P (2001). J Med Chem 44:2843–2848
Czifrák K, Páhi A, Deák S, Kiss-Szikszai A, Kövér KE, Docsa T, Gergely P, Alexacou K-M, Papakonstantinou M, Leonidas DD, Zographos SE, Chrysina ED, Somsák L (2014). Bioorg Med Chem 22:4028–4041
Szabó KE, Kun S, Mándi A, Kurtán T, Somsák L (2017). Molecules 22:1760
Czifrák K, Gyóllai V, Kövér KE, Somsák L (2011). Carbohydr Res 346:2104–2112
Acknowledgments
The authors thank the Université Claude Bernard Lyon 1 and the CNRS for financial support. MP is grateful to the Ministère de l’Enseignement supérieur et de la Recherche for a PhD stipend.
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Pommier, M., Vidal, S. (2019). Anomeric Spiro-Annulated Glycopyranosides: An Overview of Synthetic Methodologies and Biological Applications. In: Somsák, L. (eds) Carbohydrate-spiro-heterocycles. Topics in Heterocyclic Chemistry, vol 57. Springer, Cham. https://doi.org/10.1007/7081_2019_33
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DOI: https://doi.org/10.1007/7081_2019_33
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