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 |
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Hauptverfasser: | , |
Format: | Artikel |
Sprache: | eng |
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Online-Zugang: | Volltext |
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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. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.6b01985 |