Issue 6, 2014

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

Abstract

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.

Graphical abstract: De novo asymmetric synthesis of the mezzettiaside family of natural products via the iterative use of a dual B-/Pd-catalyzed glycosylation

Supplementary files

Article information

Article type
Edge Article
Submitted
25 Feb 2014
Accepted
14 Mar 2014
First published
17 Mar 2014

Chem. Sci., 2014,5, 2230-2234

Author version available

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

S. O. Bajaj, E. U. Sharif, N. G. Akhmedov and G. A. O'Doherty, Chem. Sci., 2014, 5, 2230 DOI: 10.1039/C4SC00593G

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