Novel Bis-C,C-Glycosyl Derivatives: C-Glycosides of Heptulosonic Acids and Their Spirocyclization

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Novel Bis-C,C-Glycosyl Derivatives: C-Glycosides of Heptulosonic Acids and Their Spirocyclization

Sándor Kun 1 , Nándor Kánya 1 , Nóra Magos 1 , László Somsák 1

1 Department of Organic Chemistry, University of Debrecen, Debrecen, Hungary

Several bioactive natural and synthetic compounds bear spirocyclic units. Synthesis of this motif is still a great challenge, especially on a carbohydrate framework. Natural anomeric spirocyclic compounds such as the herbicide hydantocidin [1] and the papulacandins [2] with antifungal activity are well known, other synthetic compounds show glycosidase [3], glycogen phosphorylase [4] and SGLT2 inhibition [5]. A representative from the latter group has been marketed recently for the treatment of type 2 diabetes mellitus.

C-Glycosyl derivatives of ulosonic acids are scarcely known in the literature, such type of structures are limited only to the 3-deoxy type sialic acid derivatives. Herein we report a systematic study on the synthesis of bis-C,C-glycopyranosyl compounds from fully substituted heptulosonic acids followed by cyclization to novel spirocycles. From per-O-acylated (ulopyranosyl bromide)onic acid derivatives (1) further glycosyl donors (2) were prepared with various leaving groups and anomeric configurations and the ionic and radical reactions of 1 and 2 were investigated towards bis-C,C-glycosyl derivatives 3. Transformations of the anomeric C-substituents and cyclization steps led to spirocycles 4 with five and six membered heterorings.

Figure 1. Synthesis and spirocyclization of bis-C,C-glycosyl derivatives

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Tite, T.; Tomas, L.; Docsa, T.; Gergely, P.; Kovensky, J.; Gueyrard, D.; Wadouachi, A. Synthesis of N-aryl spiro-sulfamides as potential glycogen phosphorylase inhibitors. Tetrahedron Lett. 2012, 53, 959-961.

Somsák, L. Glucose derived inhibitors of glycogen phosphorylase. Compt. Rend. Chimie 2011, 14, 211-223.

Aguillón, A. R.; Mascarello, A.; Segretti, N. D.; de Azevedo, H. F. Z.; Guimaraes, C. R. W.; Miranda, L. S. M.; de Souza, R. O. M. A. Synthetic Strategies toward SGLT2 Inhibitors. Organic Process Research & Development 2018, 22, 467-488.

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