title: Total Synthesis of Aquatolide.
abstract: A total synthesis of the sesquiterpene lactone aquatolide has been accomplished. The central step is an intramolecular [2 + 2]-photocycloaddition of an allene onto an α,β-unsaturated δ-lactone. Other key steps are an intramolecular Horner-Wadsworth-Emmons reaction to close the lactone and an intramolecular Mukaiyama-type aldol reaction to cyclize the eight-membered ring. Racemic aquatolide has been resolved using preparative HPLC.
authors.affiliation: Van't Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1098 XH Amsterdam, The Netherlands.
authors.forename: Jordy M
authors.initials: JM
authors.lastname: Saya
authors.affiliation: Van't Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1098 XH Amsterdam, The Netherlands.
authors.forename: Klaas
authors.initials: K
authors.lastname: Vos
authors.affiliation: Van't Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1098 XH Amsterdam, The Netherlands.
authors.forename: Roel A
authors.initials: RA
authors.lastname: Kleinnijenhuis
authors.affiliation: Van't Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1098 XH Amsterdam, The Netherlands.
authors.forename: Jan H
authors.initials: JH
authors.lastname: van Maarseveen
authors.affiliation: Van't Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1098 XH Amsterdam, The Netherlands.
authors.forename: Steen
authors.initials: S
authors.lastname: Ingemann
authors.affiliation: Van't Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1098 XH Amsterdam, The Netherlands.
authors.forename: Henk
authors.initials: H
authors.lastname: Hiemstra
mesh_terms: D019659:Asteraceae / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D003500:Cyclization; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D055668:Photochemical Processes; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007783:Lactones; D012717:Sesquiterpenes; C580554:aquatolide