title: Total synthesis of brevisamide.
abstract: A convergent synthesis of brevisamide (1) is described based on the application of the crotyl silane-based [4 + 2]-annulation used for the preparation of the advanced oxygenated tetrahydropyran intermediate 2. The side chain bearing a conjugated (E,E)-diene was efficiently constructed under modified Negishi cross-coupling conditions.
authors.affiliation: Department of Chemistry, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
authors.forename: Jihoon
authors.initials: J
authors.lastname: Lee
authors.forename: James S
authors.initials: JS
authors.lastname: Panek
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D011714:Pyrans; D013237:Stereoisomerism; D000095702:Polyether Toxins
chemical_list: D000470:Alkaloids; D005231:Fatty Acids, Unsaturated; D011714:Pyrans; C532303:brevisamide; D000095702:Polyether Toxins