Construction of β-Mannosidic Bonds via Gold(I)-Catalyzed Glycosylations with Mannopyranosyl<i>ortho</i>-Hexynylbenzoates and Its Application in Synthesis of Acremomannolipin A
作者:Peng Sun、Peng Wang、Yongzhen Zhang、Xiuli Zhang、Cong Wang、Shaojing Liu、Jinjie Lu、Ming Li
DOI:10.1021/acs.joc.5b00140
日期:2015.4.17
A mild and convenient protocol for direct synthesis of beta-mannosides has been developed. Glycosylation of 4,6-O-benzylidene-protected mannosyl ortho-hexynylbenzoates with various alcohol acceptors catalyzed by gold(I) complex proceeded smoothly at 0 degrees C to room temperature and afforded the corresponding beta-mannoside in high yield and satisfactory stereoselectivity. This reaction was applied to the total synthesis of acremomannolipin A and its analogue.