title: Total synthesis of (+)-ent-cyclizidine: absolute configurational confirmation of antibiotic M146791.
abstract: The first total synthesis of the enantiomer of the indolizidine alkaloid, cyclizidine, was accomplished from readily available d-serine as the starting chiron. The relevant key reactions involve the stereocontrolled construction of the indolizidine ring system with the required functionality and further elaboration to install the cyclopropyl dienyl side chain. With this total synthesis, the absolute configuration of the natural product based on a redetermination of its X-ray structure has been confirmed.
authors.affiliation: Department of Chemistry, Université de Montréal, Montreal, QC, Canada. stephen.hanessian@umontreal.ca
authors.forename: Stephen
authors.initials: S
authors.lastname: Hanessian
authors.forename: Udaykumar
authors.initials: U
authors.lastname: Soma
authors.forename: Stéphane
authors.initials: S
authors.lastname: Dorich
authors.forename: Benoît
authors.initials: B
authors.lastname: Deschênes-Simard
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D054836:Indolizidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D007212:Indolizines / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D012694:Serine / Q000031:analogs & derivatives / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000900:Anti-Bacterial Agents; D054836:Indolizidines; D007212:Indolizines; C557937:ent-cyclizidine; D012694:Serine; C043278:indolizomycin