title: Synthesis and the absolute configuration of both enantiomers of 4,5-dihydroxy-3-(formyl)cyclopent-2-enone acetonide as a new chiral building block for prostanoid synthesis.
abstract: The synthesis of both enantiomers of 4,5-dihydroxy-3-(formyl)cyclopent-2-enone acetonide (5) was accomplished in five steps starting from meso-tartaric acid (6). The key steps involved are preparation of the isopropylidene protected 3-[(dimethoxyphosphoryl)methyl]-4,5-dihydroxycyclopent-2-enone (9), resolution of the diastereoisomeric products 10 of the Horner reaction of racemic 9 with (R)-glyceraldehyde acetonide and the final regioselective ozonolysis of the exocyclic carbon–carbon double bond of the separated dienones 10 leading to both enantiomeric title compounds 5. The absolute configuration of both enantiomers was initially assigned based on the comparison of the chiroptical properties obtained from the DFT calculations with the experimental data and finally confirmed by X-ray analysis.
authors.affiliation: Department of Heteroorganic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza Str. 112, 90-363 Łódź, Poland. remzur@cbmm.lodz.pl.
authors.forename: Beata
authors.initials: B
authors.lastname: Łukasik
authors.forename: Marian
authors.initials: M
authors.lastname: Mikołajczyk
authors.forename: Grzegorz
authors.initials: G
authors.lastname: Bujacz
authors.forename: Remigiusz
authors.initials: R
authors.lastname: Żurawiński
mesh_terms: D000085:Acetates / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003517:Cyclopentanes / Q000737:chemistry*; D008968:Molecular Conformation; D011453:Prostaglandins / Q000138:chemical synthesis*; D011789:Quantum Theory; D013237:Stereoisomerism; D013644:Tartrates / Q000737:chemistry*
chemical_list: D000085:Acetates; D003517:Cyclopentanes; D011453:Prostaglandins; D013644:Tartrates; C029768:tartaric acid