Divergent Total Syntheses of Rhodomyrtosones A and B

Divergent Total Syntheses of Rhodomyrtosones A and B

Herein, we report total syntheses of the tetramethyldihydroxanthene natural product rhodomyrtosone B and the related bis-furan β-triketone natural product rhodomyrtosone A. Nickel-(II)-catalyzed 1,4-conjugate addition of an α-alkylidene-β-dicarbonyl substrate was developed to access the congener rho...

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Veröffentlicht in:Journal of organic chemistry 2015-10, Vol.80 (19), p.9584-9591
Hauptverfasser: Gervais, Anais, Lazarski, Kiel E, Porco, John A
Format: Artikel
Sprache:eng
Schlagworte:
Biological Products
Catalysis
Cyclization
Furans - chemistry
Heterocyclic Compounds, 3-Ring - chemical synthesis
Heterocyclic Compounds, 3-Ring - chemistry
Ketones - chemistry
Molecular Structure
Nickel
Stereoisomerism
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Beschreibung
Zusammenfassung:Herein, we report total syntheses of the tetramethyldihydroxanthene natural product rhodomyrtosone B and the related bis-furan β-triketone natural product rhodomyrtosone A. Nickel-(II)-catalyzed 1,4-conjugate addition of an α-alkylidene-β-dicarbonyl substrate was developed to access the congener rhodomyrtosone B, and oxygenation of the same monoalkylidene derivative followed by cyclization was employed to obtain the bis-furan natural product rhodomyrtosone A.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b01570