title: An N-acyliminium cyclization approach to a total synthesis of (+)-cylindricine C.
abstract: [reaction: see text] Details of problems and solutions encountered during the development of an enantioselective total synthesis of (+)-cylindricine C are described here. The total synthesis itself was accomplished in 8 steps, featuring an N-acyliminium cyclization strategy, the seldom-used Wharton rearrangement, and a key epimerization at C5.
authors.affiliation: Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
authors.forename: Jia
authors.initials: J
authors.lastname: Liu
authors.forename: Jacob J
authors.initials: JJ
authors.lastname: Swidorski
authors.forename: Scott D
authors.initials: SD
authors.lastname: Peters
authors.forename: Richard P
authors.initials: RP
authors.lastname: Hsung
mesh_terms: D000215:Acylation; D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006575:Heterocyclic Compounds, 3-Ring; D007097:Imines; D015363:Quinolones; C485391:cylindricine C