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Spiroketal Phthalane C-Glycosides: Synthesis of Papulacandins and SGLT2 Inhibitors

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Carbohydrate-spiro-heterocycles

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 57))

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Abstract

Spiroketals are important structural motifs found in diverse natural products, many of which display unique biological activity. Among them, spiroketal phthalane C-glycosides, in which a phthalane ring and sugar unit form a spiroketal framework, have garnered enormous attention from wide research areas because such a fascinating spirocycle motif is found in antibiotic natural products, i.e., papulacandins and their relatives. Moreover, recent reports from pharmaceutical researchers have revealed that spiroketal phthalane C-glycosides are potent drug candidates for type 2 diabetes. Accordingly, the efficient and selective construction of the spiroketal phthalane C-glycoside motif is an important research objective in synthetic organic chemistry. In this chapter, recent advances in the synthesis of spiroketal phthalane C-glycosides will be discussed.

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  1. Department of Basic Medicinal Sciences, Graduate School of Pharmaceutical Sciences, Nagoya University, Nagoya, Japan

    Yoshihiko Yamamoto

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

    László Somsák

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Yamamoto, Y. (2019). Spiroketal Phthalane C-Glycosides: Synthesis of Papulacandins and SGLT2 Inhibitors. In: Somsák, L. (eds) Carbohydrate-spiro-heterocycles. Topics in Heterocyclic Chemistry, vol 57. Springer, Cham. https://doi.org/10.1007/7081_2018_27

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