title: The first synthesis of (-)-isoambreinolide, (+)-vitexifolin D and (+)-vitedoin B.
abstract: A very efficient method for synthesizing spirolactones is reported. Treatment of δ,ε-unsaturated carboxylic acids with iodine and triphenylphosphine under mild conditions leads to the corresponding spiro γ-lactones in high yield and with complete stereoselectivity. Utilizing this, the first synthesis of the terpene spirolactones (-)-isoambreinolide, (+)-vitexifolin D and (+)-vitedoin B has been achieved.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071 Granada, Spain. rachid@ugr.es eamr@ugr.es.
authors.forename: Hanane
authors.initials: H
authors.lastname: Bouanou
authors.forename: Rubén
authors.initials: R
authors.lastname: Tapia
authors.forename: M José
authors.initials: MJ
authors.lastname: Cano
authors.forename: Jose M
authors.initials: JM
authors.lastname: Ramos
authors.forename: Esteban
authors.initials: E
authors.lastname: Alvarez
authors.forename: Ettahir
authors.initials: E
authors.lastname: Boulifa
authors.forename: Abdelaziz
authors.initials: A
authors.lastname: Dahdouh
authors.forename: Ahmed I
authors.initials: AI
authors.lastname: Mansour
authors.forename: Ramón
authors.initials: R
authors.lastname: Alvarez-Manzaneda
authors.forename: Rachid
authors.initials: R
authors.lastname: Chahboun
authors.forename: Enrique
authors.initials: E
authors.lastname: Alvarez-Manzaneda
mesh_terms: D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; D007783:Lactones; D013141:Spiro Compounds; C497096:vitedoin B