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

Chemical Science
Sumit O BajajGeorge A O'Doherty

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 to 22 longest linear steps and required only 41 total steps to prepare the entire family of mezzettiasides.

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Citations

May 12, 2016·The Journal of Organic Chemistry·Zhilong Li, Rongbiao Tong
Aug 18, 2016·Journal of the American Chemical Society·Kyan A D'Angelo, Mark S Taylor
Mar 21, 2017·Chemistry, an Asian Journal·Wangze SongWeiping Tang
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Jan 1, 2016·RSC Advances·Arun K Ghosh, Margherita Brindisi
Nov 5, 2020·Organic & Biomolecular Chemistry·Eike B Bauer
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Apr 9, 2021·The Journal of Organic Chemistry·Naoyuki ShimadaKazuishi Makino
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