title: Stereoselective total synthesis and absolute configuration of the natural decanolides (-)-microcarpalide and (+)-lethaloxin. Identity of (+)-lethaloxin and (+)-pinolidoxin.
abstract: [reaction: see text] Convergent, stereoselective syntheses of the pharmacologically active, naturally occurring lactones (-)-microcarpalide and (+)-lethaloxin have been achieved from the commercially available, chiral reagents (R)-glycidol, (S,S)-tartaric acid, and d-ribose as the starting materials. These syntheses have further served to establish the hitherto unknown absolute configuration of (+)-lethaloxin and to show its identity with (+)-pinolidoxin.
authors.affiliation: Departamento de Química Inorgánica y Orgánica, Universidad Jaume I, E-12071 Castellón, Spain.
authors.forename: Jorge
authors.initials: J
authors.lastname: García-Fortanet
authors.forename: Juan
authors.initials: J
authors.lastname: Murga
authors.forename: Eva
authors.initials: E
authors.lastname: Falomir
authors.forename: Miguel
authors.initials: M
authors.lastname: Carda
authors.forename: J Alberto
authors.initials: JA
authors.lastname: Marco
mesh_terms: D000473:Alkanes / Q000138:chemical synthesis / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000473:Alkanes; D000475:Alkenes; D006573:Heterocyclic Compounds, 1-Ring; D007659:Ketones; C442266:microcarpalide; C410769:pinolidoxin