Construction of β-Mannosidic Bonds via Gold(I)-Catalyzed Glycosylations with Mannopyranosyl ortho-Hexynylbenzoates and Its Application in Synthesis of Acremomannolipin A

• DOI: 10.1021/acs.joc.5b00140
• Publication Date: 2015-03-20T17:40:58Z
• Authors: Peng Sun; Peng Wang; Yongzhen Zhang; Xiuli Zhang; Cong Wang; Shaojing Liu; Jinjie Lu; Ming Li
• Keywords: Glycosylation; Molecular Structure; Mannosides; Gold; Glycolipids; Benzoates; 01 natural sciences; Catalysis; 0104 chemical sciences

A mild and convenient protocol for direct synthesis of β-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 °C to room temperature and afforded the corresponding β-mannoside in high yield and satisfactory stereoselectivity. This reaction was applied to the total synthesis of acremomannolipin A and its analogue.