title: Stereoselective route to oxetanocin carbocyclic analogues based on a [2 + 2] photocycloaddition to a chiral 2(5H)-furanone.
abstract: The synthesis of the trisubstituted cyclobutane 7, which is a suitable precursor for the preparation of oxetanocin carbocyclic analogues, is described. The key step involves a regio- and diastereoselective [2 + 2] photochemical reaction of ketene diethyl acetal with (S)-5-pivaloyloxymethyl-2(5H)-furanone, 3. As an application of this methodology, (-)-cyclobut-A has been prepared from the intermediate 7.
authors.affiliation: Departament de Química, Universitat Autonoma de Barcelona, 08193 Bellaterra, Spain.
authors.forename: Albert
authors.initials: A
authors.lastname: Rustullet
authors.forename: Ramon
authors.initials: R
authors.lastname: Alibés
authors.forename: Pedro
authors.initials: P
authors.lastname: de March
authors.forename: Marta
authors.initials: M
authors.lastname: Figueredo
authors.forename: Josep
authors.initials: J
authors.lastname: Font
mesh_terms: D000225:Adenine / Q000031:analogs & derivatives* / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D010777:Photochemistry; D013237:Stereoisomerism
chemical_list: D005663:Furans; C051061:oxetanocin; D000225:Adenine