title: A concise synthetic approach to the sorbicillactones: total synthesis of sorbicillactone A and 9-epi-sorbicillactone A.
abstract: A concise (12 step) total synthesis of sorbicillactone A and 9-epi-sorbicillactone A is reported. Unlike typical routes to the sorbicillinoids, this strategy does not start from sorbicillin and allows for the production of the bicyclic core on a multigram scale. The intramolecular conjugate addition of a tethered malonate serves as an effective means of introducing the lactone ring and provides a synthetic handle for installing the amide nitrogen.
authors.affiliation: Department of Chemistry, University of Minnesota-Twin Cities, 207 Pleasant Street SE, Minneapolis, Minnesota 55455, USA.
authors.forename: Kelly A
authors.initials: KA
authors.lastname: Volp
authors.forename: Diane M
authors.initials: DM
authors.lastname: Johnson
authors.forename: Andrew M
authors.initials: AM
authors.lastname: Harned
mesh_terms: D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001572:Benzofurans; C500693:sorbicillactone A