title: The first total synthesis of 15-deoxy-Delta12,14-prostaglandin J2 and the unambiguous assignment of the C14 stereochemistry.
abstract: [reaction: see text] The first total synthesis of 15-deoxy-Delta12,14-prostaglandin J2 is reported. The highly unsaturated cyclopentenone prostaglandin was obtained via a silicon-tethered allenic [2 + 2 + 1] cycloaddition reaction developed in our group. In addition, the stereochemistry at C14 has been assigned unambiguously.
authors.affiliation: University of Pittsburgh, Department of Chemistry, Pittsburgh, Pennsylvania 15260, USA. kbrummon@pitt.edu
authors.forename: Kay M
authors.initials: KM
authors.lastname: Brummond
authors.forename: Peter C
authors.initials: PC
authors.lastname: Sill
authors.forename: Hongfeng
authors.initials: H
authors.lastname: Chen
mesh_terms: D002244:Carbon / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D015230:Prostaglandin D2 / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D012825:Silicon / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C477819:15-deoxyprostaglandin J2; D002244:Carbon; D015230:Prostaglandin D2; D012825:Silicon