title: Synthesis of (±)-4,5-dia-Parthenolide, an Unnatural Parthenolide Stereoisomer.
abstract: A short total synthesis of the novel unnatural parthenolide diastereomer (±)-4,5-dia-parthenolide was accomplished in 13 steps and an overall yield of 1.75% starting from commercially available (E,E)-farnesol. The challenging isopropenyl side chain oxidation was regioselectively achieved via a newly developed stepwise dihydroxylation procedure, employing a Bartlett-Smith iodocarbonate cyclization followed by iodide substitution and catalytic transesterification.
authors.affiliation: Friedrich-Schiller-Universität, Institut für Organische Chemie und Makromolekulare Chemie , Humboldtstr. 10, 07743 Jena, Germany.
authors.forename: Robert R A
authors.initials: RR
authors.lastname: Freund
authors.affiliation: Friedrich-Schiller-Universität, Institut für Organische Chemie und Makromolekulare Chemie , Humboldtstr. 10, 07743 Jena, Germany.
authors.forename: Hans-Dieter
authors.initials: HD
authors.lastname: Arndt
mesh_terms: D066241:Carbon-13 Magnetic Resonance Spectroscopy; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D003500:Cyclization; D004951:Esterification; D006900:Hydroxylation; D066244:Proton Magnetic Resonance Spectroscopy; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
chemical_list: D012717:Sesquiterpenes; C002669:parthenolide