title: Total synthesis of (±)-cylindricine C.
abstract: A concise synthesis of (±)-cylindricine C and its C(13)-epimer is described. Starting from 1-octyne, cylindricine C and 13-epi-cylindricine C were prepared in 11% and 15% yields, respectively. The synthesis involves the preparation of the central tricyclic moiety via a radical α-iodoketone carboazidation/bis-reductive amination sequence. Inversion of the stereochemistry at C(13) and C(5) was efficiently achieved on late stage intermediates.
authors.affiliation: University of Bern, Department of Chemistry and Biochemistry, Freiestrasse 3, CH-3012 Bern, Switzerland.
authors.forename: Guillaume
authors.initials: G
authors.lastname: Lapointe
authors.forename: Kurt
authors.initials: K
authors.lastname: Schenk
authors.forename: Philippe
authors.initials: P
authors.lastname: Renaud
mesh_terms: D018360:Crystallography, X-Ray; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006575:Heterocyclic Compounds, 3-Ring; D015363:Quinolones; C485391:cylindricine C