title: Total synthesis of ingenol.
abstract: A total synthesis of the biologically important diterpene ingenol has been completed. Ring-closing olefin metathesis was used to construct the strained "inside-outside" tetracyclic skeleton, and a series of diastereoselective reactions were employed to complete the synthesis. Another naturally occurring ingenane, 20-deoxyingenol, has also been prepared.
authors.affiliation: Sterling Chemistry Laboratory, Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, USA.
authors.forename: Andrew
authors.initials: A
authors.lastname: Nickel
authors.forename: Toru
authors.initials: T
authors.lastname: Maruyama
authors.forename: Haifeng
authors.initials: H
authors.lastname: Tang
authors.forename: Prescott D
authors.initials: PD
authors.lastname: Murphy
authors.forename: Blake
authors.initials: B
authors.lastname: Greene
authors.forename: Naeem
authors.initials: N
authors.lastname: Yusuff
authors.forename: John L
authors.initials: JL
authors.lastname: Wood
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D013450:Sulfones / Q000737:chemistry
chemical_list: D000498:Allyl Compounds; D004224:Diterpenes; D013450:Sulfones; C008125:ingenol