Highly Enantioselective Total Synthesis of (−)-(3′S)-Lomatin and (+)-(3′S,4′R)-trans-Khellactone

Highly Enantioselective Total Synthesis of (−)-(3′S)-Lomatin and (+)-(3′S,4′R)-trans-Khellactone

Concise highly enantioselective three-step syntheses are described for (−)-(3′S)-lomatin and (+)-(3′S,4′R)-trans-khellactone from 7-hydroxycoumarin in 97% ee and in 57% and 58% overall yields, respectively, using nonaqueous enantioselective epoxidation by an iminium salt as the key step.

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Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2009-05, Vol.11 (9), p.1991-1993
Hauptverfasser: Page, Philip C. Bulman, Appleby, Louise F, Day, David, Chan, Yohan, Buckley, Benjamin R, Allin, Steven M, McKenzie, Michael J
Format: Artikel
Sprache:eng
Schlagworte:
Coumarins - chemical synthesis
Coumarins - chemistry
Crystallography, X-Ray
Molecular Structure
Stereoisomerism
Umbelliferones - chemistry
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Zusammenfassung:Concise highly enantioselective three-step syntheses are described for (−)-(3′S)-lomatin and (+)-(3′S,4′R)-trans-khellactone from 7-hydroxycoumarin in 97% ee and in 57% and 58% overall yields, respectively, using nonaqueous enantioselective epoxidation by an iminium salt as the key step.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol900444h