title: Synthesis of the cyclobutanone core of solanoeclepin A intramolecular allene butenolide photocycloaddition.
abstract: The compact tricyclic substructure of solanoeclepin A containing the cyclobutanone ring was prepared by using as the key step a highly regioselective intramolecular [2 + 2]-photocycloaddition reaction between one of the [small pi]-bonds of an allene and the CC double bond of a butenolide.
authors.affiliation: Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands.
authors.forename: Bui T B
authors.initials: BT
authors.lastname: Hue
authors.forename: Jan
authors.initials: J
authors.lastname: Dijkink
authors.forename: Sanne
authors.initials: S
authors.lastname: Kuiper
authors.forename: Kimberly K
authors.initials: KK
authors.lastname: Larson
authors.forename: Frank S
authors.initials: FS
authors.lastname: Guziec
authors.forename: Kees
authors.initials: K
authors.lastname: Goubitz
authors.forename: Jan
authors.initials: J
authors.lastname: Fraanje
authors.forename: Henk
authors.initials: H
authors.lastname: Schenk
authors.forename: Jan H
authors.initials: JH
authors.lastname: van Maarseveen
authors.forename: Henk
authors.initials: H
authors.lastname: Hiemstra
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000737:chemistry; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D003503:Cyclobutanes / Q000138:chemical synthesis / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D006586:Hexanes / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D010777:Photochemistry; D013237:Stereoisomerism
chemical_list: D001643:Bridged Bicyclo Compounds; D001952:Bridged-Ring Compounds; D003503:Cyclobutanes; D005663:Furans; D006586:Hexanes; D007659:Ketones; C431673:solanoeclepin A; C004511:butenolide; D015107:4-Butyrolactone