Total synthesis of brevisamide.
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.
Lee
Jihoon
J
Department of Chemistry, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
Panek
James S
JS
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
D000470:Alkaloids; D005231:Fatty Acids, Unsaturated; D011714:Pyrans; C532303:brevisamide; D000095702:Polyether Toxins