title: Total Synthesis of (-)-L-755,807: Establishment of Relative and Absolute Configurations.
abstract: The first total synthesis of (-)-L-755,807 and its three stereoisomers was achieved by our Horner-Wadsworth-Emmons reaction for stereoselective formation of trisubstituted olefins, highly diastereoselective Darzens condensation to construct the epoxy-γ-lactam ring, and late-stage coupling of the ring and side-chain segments for efficient convergent synthesis. This synthesis shows that the originally proposed structure of natural (-)-L-755,807 was incorrect and establishes its relative and absolute configurations.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Meiji Pharmaceutical University , 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan.
authors.forename: Kosaku
authors.initials: K
authors.lastname: Tanaka
authors.affiliation: Graduate School of Pharmaceutical Sciences, Meiji Pharmaceutical University , 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan.
authors.forename: Kenichi
authors.initials: K
authors.lastname: Kobayashi
authors.affiliation: Graduate School of Pharmaceutical Sciences, Meiji Pharmaceutical University , 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Kogen
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D004852:Epoxy Compounds; C000611116:L-755,807; D007769:Lactams