Synthesis of (±)-4,5-dia-Parthenolide, an Unnatural Parthenolide Stereoisomer

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...

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Veröffentlicht in:Journal of organic chemistry 2016-11, Vol.81 (22), p.11009-11016
Hauptverfasser: Freund, Robert R. A, Arndt, Hans-Dieter
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b01985