title: A formal enantioselective total synthesis of FR901483.
abstract: A formal enantioselective total synthesis of the potent immunosuppressant FR901483 (1) has been accomplished. Our approach features the use of chiron 6 as the starting material, the application of the one-pot amide reductive bisalkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diastereoselective intramolecular aldol reaction to build the bridged ring, and ring closing metathesis 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: Hong-Kui
authors.initials: HK
authors.lastname: Zhang
authors.forename: Xiao-Er
authors.initials: XE
authors.lastname: Xia
authors.forename: Pei-Qiang
authors.initials: PQ
authors.lastname: Huang
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D007166:Immunosuppressive Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; C098358:FR 901483; D007166:Immunosuppressive Agents; D009943:Organophosphorus Compounds; C116609:3-hydroxybutanal