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Erschienen in:
Anomeric Spiro-Annulated Glycopyranosides: An Overview of Synthetic Methodologies and Biological Applications Kapitel lesen Erstes Kapitel lesen

2019 | OriginalPaper | Buchkapitel

Cycloaddition Reactions of Sugar-Based Olefins, Nitrones and Nitrile Oxides: En Route to Saccharidic Spiroisoxazoli(di)nes

verfasst von : Nadia Pellegrini-Moïse, Mylène Richard

Erschienen in: Carbohydrate-spiro-heterocycles

Verlag: Springer International Publishing

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Abstract

Isoxazoline- and isoxazolidine-containing compounds are privileged structures of interest, notably in synthetic and medicinal chemistry. These heterocycles can be obtained by 1,3-dipolar cycloaddition reactions between an olefin and a nitrile oxide or a nitrone. This reaction generates one C–C and one C–O bond and up to three chiral centres in one step. In the present chapter, we aim to summarize and discuss reports of these cycloadditions on sugar olefins, with a focus on exo-methylene sugars or activated exo-glycals, leading to saccharidic spiroisoxazoli(di)nes with high regio- and stereocontrol. Additional examples of cycloaddition reactions involving chiral nitrone, sugar nitrile oxide, sugar nitrone and two chiral sugar partners will also be discussed. Due to the importance of the spiro structure in several biologically active compounds, these spiroheterocycles can be regarded as spironucleoside analogues, mimics of natural building blocks or multicyclic sugar scaffolds suitable for selective derivatization. Some of them thus showed promising biological properties as antibacterial agents or enzyme inhibitors. Moreover, the labile nature of the N–O bond in the isoxazolidine ring makes it an attractive target for synthetic chemists. The reactivity of this scaffold has therefore been widely studied, and the cycloadducts have been converted to other classes of compounds of interest. Examples of the biological relevance and synthetic use and reactivity of these spiro-sugars will be given in this chapter.

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Vorheriges Kapitel Anomeric Spiro-Annulated Glycopyranosides: An Overview of Synthetic Methodologies and Biological Applications
Nächstes Kapitel Carbohydrate Spiro-heterocycles via Radical Chemistry
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Metadaten
Titel
Cycloaddition Reactions of Sugar-Based Olefins, Nitrones and Nitrile Oxides: En Route to Saccharidic Spiroisoxazoli(di)nes
verfasst von
Nadia Pellegrini-Moïse
Mylène Richard
Copyright-Jahr
2019
Buch
Carbohydrate-spiro-heterocycles

Print ISBN: 978-3-030-31941-0

Electronic ISBN: 978-3-030-31942-7

Copyright-Jahr: 2019

DOI
https://doi.org/10.1007/7081_2019_28

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