title: Construction of β-mannosidic bonds via gold(I)-catalyzed glycosylations with mannopyranosyl ortho-hexynylbenzoates and its application in synthesis of acremomannolipin A.
abstract: 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.
authors: †Key Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003 Shandong, P. R. China.
authors: Peng
authors: P
authors: Sun
authors: †Key Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003 Shandong, P. R. China.
authors: Peng
authors: P
authors: Wang
authors: †Key Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003 Shandong, P. R. China.
authors: Yongzhen
authors: Y
authors: Zhang
authors: †Key Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003 Shandong, P. R. China.
authors: Xiuli
authors: X
authors: Zhang
authors: †Key Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003 Shandong, P. R. China.
authors: Cong
authors: C
authors: Wang
authors: †Key Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003 Shandong, P. R. China.
authors: Shaojing
authors: S
authors: Liu
authors: †Key Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003 Shandong, P. R. China.
authors: Jinjie
authors: J
authors: Lu
authors: †Key Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003 Shandong, P. R. China.|‡State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Science, Shanghai, 201203, P. R. China.
authors: Ming
authors: M
authors: Li
mesh_terms: D001565:Benzoates / Q000737:chemistry*; D002384:Catalysis; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry*; D006031:Glycosylation; D006046:Gold / Q000737:chemistry*; D008362:Mannosides / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D001565:Benzoates; D006017:Glycolipids; D008362:Mannosides; C579014:acremomannolipin A; D006046:Gold