Exploring Chemical Diversity of Epoxyquinoid Natural Products:  Synthesis and Biological Activity of (−)-Jesterone and Related Molecules

Exploring Chemical Diversity of Epoxyquinoid Natural Products:  Synthesis and Biological Activity of (−)-Jesterone and Related Molecules

Enantioselective syntheses of the potent antifungal agent (−)-jesterone, its hydroxy epimer, and a dimeric quinone epoxide derivative are reported. The synthesis involves diastereoselective epoxidation of a chiral quinone monoketal derivative and regio- and stereoselective reduction of a quinone epo...

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Veröffentlicht in:Organic letters 2001-05, Vol.3 (11), p.1649-1652
Hauptverfasser: Hu, Yongbo, Li, Chaomin, Kulkarni, Bheemashankar A, Strobel, Gary, Lobkovsky, Emil, Torczynski, Richard M, Porco, John A
Format: Artikel
Sprache:eng
Schlagworte:
Alkenes - chemical synthesis
Antifungal Agents - chemical synthesis
Antifungal Agents - chemistry
Crystallography, X-Ray
Epoxy Compounds - chemical synthesis
Indicators and Reagents
Models, Molecular
Stereoisomerism
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Zusammenfassung:Enantioselective syntheses of the potent antifungal agent (−)-jesterone, its hydroxy epimer, and a dimeric quinone epoxide derivative are reported. The synthesis involves diastereoselective epoxidation of a chiral quinone monoketal derivative and regio- and stereoselective reduction of a quinone epoxide intermediate.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0159367