title: Toward the racemic total synthesis of hederacines A and B: construction of an advanced tricyclic intermediate.
abstract: Progress toward the total synthesis of hederacines A and B is described. Our approach involves an allylic cyanate-to-isocyanate rearrangement, eneyne ring-closing metathesis, and a transannular reaction between the C-5 amino group and the C-12 position of the perhydroazuleno[5,6-b]furanone intermediate.
authors.affiliation: School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, Horinouchi, Hachioji, Tokyo 192-0392, Japan.
authors.forename: Miho
authors.initials: M
authors.lastname: Yamashita
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Yamashita
authors.forename: Sakae
authors.initials: S
authors.lastname: Aoyagi
mesh_terms: D000588:Amines / Q000737:chemistry; D001372:Aza Compounds / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D014326:Tropanes / Q000138:chemical synthesis*
chemical_list: D000588:Amines; D001372:Aza Compounds; D006575:Heterocyclic Compounds, 3-Ring; D014326:Tropanes; C559806:hederacine A; C559807:hederacine B