title: Total synthesis of (±)-Gelsemoxonine.
abstract: Gelsemoxonine (1) is a Gelsemium alkaloid incorporating an unusual azetidine. Its total synthesis was achieved employing a novel ring contraction of a spirocyclopropane isoxazolidine to furnish a β-lactam intermediate. This β-lactam ring was further elaborated into the azetidine of Gelsemoxonine. In addition, the synthesis includes a highly diastereoselective reductive Heck cyclization for the installation of the oxindole ring system as well as a directed hydrosilylation of an alkyne to access the ethyl ketone of the natural product.
authors.affiliation: Eidgenössische Technische Hochschule Zürich, HCI H335, 8093 Zürich, Switzerland.
authors.forename: Stefan
authors.initials: S
authors.lastname: Diethelm
authors.forename: Erick M
authors.initials: EM
authors.lastname: Carreira
mesh_terms: D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids; C478255:gelsemoxonine