Denovo asymmetric synthesis of the mezzettiaside family of natural products via the iterative use of a dual B-/Pd-catalyzed glycosylationElectronic supplementary information (ESI) available: Experimental procedures, 1H and 13C NMR spectra and correlation studies. See DOI: 10.0000/c4sc00593g

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
Main Authors Bajaj, Sumit O, Sharif, Ehesan U, Akhmedov, Novruz G, O'Doherty, George A
Format Journal Article
LanguageEnglish
Published 07.05.2014
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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. Synthesis of the mezzettiaside family of natural products via the iterative use of a dual nucleophilic boron/electrophilic Pd-catalyzed glycosylation.
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H and
C NMR spectra and correlation studies. See DOI
10.0000/c4sc00593g
Electronic supplementary information (ESI) available: Experimental procedures
ISSN:2041-6520
2041-6539
DOI:10.1039/c4sc00593g