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Issue 9, 2015
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O-Glycosylation methods in the total synthesis of complex natural glycosides

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Abstract

Covering: 1994–2015

The total syntheses of 33 complex natural O-glycosides, such as the glycosides of macrocyclic lactones/lactams, enediynes, angucyclines, and anthracyclines, are highlighted, with a major focus being placed on the O-glycosylation reactions which connect the saccharides and the aglycones. These successful O-glycosylation reactions employ such donors as glycosyl bromides, fluorides, iodides, trichloroacetimidates, N-phenyl trifluoroacetimidates, thioglycosides, sulfoxides, heteroaryl thioglycosides, 1-hydroxyl sugars, 1-O-acetates, and ortho-alkynylbenzoates. Each synthesis is depicted starting from the O-glycosylation of the aglycone (or its precursor); the glycosylation conditions and outcomes (yields and stereoselectivities) are discussed, and the subsequent transformations toward the final target, including the elongation of the glycan, the elaboration of the aglycone, and the protecting group manipulations are also given in detail.

Graphical abstract: O-Glycosylation methods in the total synthesis of complex natural glycosides

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Publication details

The article was received on 30 Mar 2015 and first published on 12 Jun 2015


Article type: Review Article
DOI: 10.1039/C5NP00033E
Citation: Nat. Prod. Rep., 2015,32, 1331-1355
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    O-Glycosylation methods in the total synthesis of complex natural glycosides

    Y. Yang, X. Zhang and B. Yu, Nat. Prod. Rep., 2015, 32, 1331
    DOI: 10.1039/C5NP00033E

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