title: Total synthesis of (-)-13-oxyingenol and its natural derivative.
abstract: Ring functionalization: the total synthesis of a natural derivative of (-)-13-oxyingenol, a potent anti-HIV diterpenoid, is reported. The key steps in this synthesis include a ring-closing olefin metathesis and a Mislow-Evans-type [2,3]-sigmatropic rearrangement. This synthesis provides access to (-)-13-oxyingenol and its natural derivative in 21 steps from a synthetic intermediate previously prepared by Kigoshi and co-workers.
authors.affiliation: Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Japan.
authors.forename: Takayuki
authors.initials: T
authors.lastname: Ohyoshi
authors.forename: Shota
authors.initials: S
authors.lastname: Funakubo
authors.forename: Yamato
authors.initials: Y
authors.lastname: Miyazawa
authors.forename: Keisuke
authors.initials: K
authors.lastname: Niida
authors.forename: Ichiro
authors.initials: I
authors.lastname: Hayakawa
authors.forename: Hideo
authors.initials: H
authors.lastname: Kigoshi
mesh_terms: D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C559803:13-oxyingenol; D004224:Diterpenes; C008125:ingenol