Denovoasymmetric synthesis of the mezzettiaside family of natural products viathe 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...

Full description

Saved in:
Bibliographic Details
Published in:Chemical science (Cambridge) 2014-05, Vol.5 (6), p.2230-2234
Main Authors: Bajaj, Sumit O, Sharif, Ehesan U, Akhmedov, Novruz G, O'Doherty, George A
Format: Article
Language:English
Subjects:
Boron
Catalysts
Natural products
Palladium
Synthesis
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
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 novoapproach 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