RCM approaches toward the diastereoselective synthesis of vicinal trans-diaminocyclitols from L-serine.
Starting from L-serine, the asymmetric synthesis of four diaminocyclitol derivatives as sugar-based glycosidase inhibitors has been achieved using ring-closing metathesis (RCM) as a key step. Introduction of vicinal trans-diamino functionality onto the acyclic precursors was accomplished by highly diastereoselective addition of Grignard reagent to imine, and the elaboration of polyhydroxylic groups was effected via diastereoselective olefin epoxidation or dihydroxylation. The absolute configurations of final products were confirmed by 2D NMR studies.
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.
Xin
X
Cong
Qing-Jiang
QJ
Liao
Zhu-Jun
ZJ
Yao
D002384:Catalysis; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D006595:Hexosamines / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012694:Serine / Q000737:chemistry*; D013237:Stereoisomerism
D004791:Enzyme Inhibitors; D006595:Hexosamines; D007202:Indicators and Reagents; D012694:Serine; D006026:Glycoside Hydrolases