Gold(I)-Catalyzed Intermolecular Rearrangement Reaction of Glycosyl Alkynoic β-Ketoesters for the Synthesis of 4- O-Glycosylated 2-Pyrones

Rongkun Liu; Xiaoqian Li; Xiaona Li; Jiazhe Wang; You Yang

doi:10.1021/acs.joc.9b01582

Gold(I)-Catalyzed Intermolecular Rearrangement Reaction of Glycosyl Alkynoic β-Ketoesters for the Synthesis of 4- O-Glycosylated 2-Pyrones

J Org Chem. 2019 Nov 1;84(21):14141-14150. doi: 10.1021/acs.joc.9b01582. Epub 2019 Oct 4.

Authors

Rongkun Liu¹, Xiaoqian Li¹, Xiaona Li¹, Jiazhe Wang¹, You Yang¹

Affiliation

¹ Shanghai Key Laboratory of New Drug Design, School of Pharmacy , East China University of Science and Technology , 130 Meilong Road , Shanghai 200237 , China.

PMID: 31565928
DOI: 10.1021/acs.joc.9b01582

Abstract

A new gold(I)-catalyzed rearrangement reaction with glycosyl alkynoic β-ketoesters as substrates is developed. The rearrangement reactions under the catalysis of PPh₃AuOTf proceeded smoothly to afford a range of 4-O-glycosylated 2-pyrones. Based on the isolation of the 4-hydroxy-2-pyrone derivative generated from the departure of the leaving group and the competitive reaction, a plausible mechanism of the gold(I)-catalyzed intermolecular rearrangement reactions is proposed.

Publication types

Research Support, Non-U.S. Gov't