title: Enantioselective total syntheses of (-)-FR901483 and (+)-8-epi-FR901483.
abstract: The enantioselective total syntheses of the potent immunosuppressant FR901483 (1) and its 8-epimer (47) have been accomplished. Our approach features the use of building block 6 as the chiron, the application of the one-pot amide reductive bis-alkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diastereoselective intramolecular aldol reaction to build the bridged ring, and RCM to form the 3-pyrrolin-2-one ring.
authors.affiliation: Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, PR China.
authors.forename: Hao-Hua
authors.initials: HH
authors.lastname: Huo
authors.forename: Xiao-Er
authors.initials: XE
authors.lastname: Xia
authors.forename: Hong-Kui
authors.initials: HK
authors.lastname: Zhang
authors.forename: Pei-Qiang
authors.initials: PQ
authors.lastname: Huang
mesh_terms: D000478:Alkylation; D001372:Aza Compounds / Q000737:chemistry*; D007166:Immunosuppressive Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001372:Aza Compounds; C098358:FR 901483; D007166:Immunosuppressive Agents; D009943:Organophosphorus Compounds