title: Synthetic studies on chartelline C: stereoselective construction of the core skeleton.
abstract: What a core-ker! The title synthesis was achieved using a route featuring an intramolecular Mitsunobu reaction of a nosyl amide, stereoselective construction of the β-lactam, and formation of an enamide moiety by selenoxide elimination. The stereochemistry of the alkylation for the formation of the β-lactam was controlled by a secondary hydroxy group on the ten-membered ring. SEM=2-(trimethylsilyl)ethoxymethyl; TBS=tert-butyldimethylsilyl.
authors.affiliation: Graduate School of Pharmaceutical Sciences, University of Tokyo, Tokyo, Japan.
authors.forename: Kotaro
authors.initials: K
authors.lastname: Iwasaki
authors.forename: Rentaro
authors.initials: R
authors.lastname: Kanno
authors.forename: Toshiharu
authors.initials: T
authors.lastname: Morimoto
authors.forename: Tohru
authors.initials: T
authors.lastname: Yamashita
authors.forename: Satoshi
authors.initials: S
authors.lastname: Yokoshima
authors.forename: Tohru
authors.initials: T
authors.lastname: Fukuyama
mesh_terms: D000478:Alkylation; D007093:Imidazoles / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D013237:Stereoisomerism; D047090:beta-Lactams / Q000737:chemistry
chemical_list: D007093:Imidazoles; D007211:Indoles; D047090:beta-Lactams; C513615:chartelline; C029899:imidazole