Denovo asymmetric synthesis of the mezzettiaside family of natural products via the iterative use of a dual B-/Pd-catalyzed glycosylation

The first synthesis of any and all members of the mezzettiaside family of natural products has been achieved. The reported synthesis features the iterative use of the Taylor catalyst in a dual nucleophilic boron/electrophilic palladium catalyzed regioselective glycosylation. In addition, the de novo...

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Bibliographic Details
Published inChemical science (Cambridge) Vol. 5; no. 6; pp. 2230 - 2234
Main Authors Bajaj, Sumit O., Sharif, Ehesan U., Akhmedov, Novruz G., O'Doherty, George A.
Format Journal Article
LanguageEnglish
Published 2014
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Summary:The first synthesis of any and all members of the mezzettiaside family of natural products has been achieved. The reported synthesis features the iterative use of the Taylor catalyst in a dual nucleophilic boron/electrophilic palladium catalyzed regioselective glycosylation. In addition, the de novo approach utilizes atomless protecting groups and the minimal use of protecting groups (2 chloroacetates for the synthesis of 10 natural products). These divergent syntheses occurred in a range of 13–22 longest linear steps and required only 41 total steps to prepare the entire family of mezzettiasides.
ISSN:2041-6520
2041-6539
DOI:10.1039/C4SC00593G