title: Synthesis of (±)-Bisavenanthramide B-6 by an Anionic Anhydride Mannich Reaction.
abstract: Bisavenanthramide B-6 (2) is a highly substituted γ-lactam derived from oat leaves. Development of a new base-promoted anhydride Mannich reaction with N-sulfonylated imines that forms the core structure of 2 in a single step is presented. Further elaboration allows for a facile one-pot double Buchwald N-arylation to install the final rings onto the densely substituted γ-lactam core. This route provides the natural product in a longest linear sequence of nine steps.
authors.affiliation: Department of Chemistry, University of California, Davis , One Shields Avenue, Davis, California 95616, United States.
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Di Maso
authors.affiliation: Department of Chemistry, University of California, Davis , One Shields Avenue, Davis, California 95616, United States.
authors.forename: Gabriella M
authors.initials: GM
authors.lastname: Nepomuceno
authors.affiliation: Department of Chemistry, University of California, Davis , One Shields Avenue, Davis, California 95616, United States.
authors.forename: Michael A
authors.initials: MA
authors.lastname: St Peter
authors.affiliation: Department of Chemistry, University of California, Davis , One Shields Avenue, Davis, California 95616, United States.
authors.forename: Haley H
authors.initials: HH
authors.lastname: Gitre
authors.affiliation: Department of Chemistry, University of California, Davis , One Shields Avenue, Davis, California 95616, United States.
authors.forename: Kevin S
authors.initials: KS
authors.lastname: Martin
authors.affiliation: Department of Chemistry, University of California, Davis , One Shields Avenue, Davis, California 95616, United States.
authors.forename: Jared T
authors.initials: JT
authors.lastname: Shaw
mesh_terms: D000812:Anhydrides / Q000138:chemical synthesis* / Q000737:chemistry; D000838:Anions / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000812:Anhydrides; D000838:Anions; D007769:Lactams; C000610798:bisavenanthramide B-6