title: Highly efficient and diastereoselective synthesis of (+)-lineatin.
abstract: [reaction: see text] A linear sequence was used to synthesize (+)-lineatin in 14 steps and 14% overall yield from a homochiral 2(5H)-furanone. Key steps of this synthetic approach feature the diastereoselective construction of a cyclobutene through a photochemical [2 + 2] cycloaddition and a regiocontrolled oxymercuration reaction.
authors.affiliation: Departament de Química and Servei de Ressonància Magnètica Nuclear, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain.
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
authors.forename: Marta
authors.initials: M
authors.lastname: Racamonde
authors.forename: Teodor
authors.initials: T
authors.lastname: Parella
mesh_terms: D003500:Cyclization; D008968:Molecular Conformation; D010675:Pheromones / Q000138:chemical synthesis* / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D012680:Sensitivity and Specificity; D013237:Stereoisomerism
chemical_list: D010675:Pheromones; D011714:Pyrans; C037523:lineatin