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 rhodomyrtosone B, and oxygenation of the same monoalkylidene derivative followed by cyclization was employed to obtain the bis-furan natural product rhodomyrtosone A.
Department of Chemistry, Center for Molecular Discovery (BU-CMD), Boston University , 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.
Anais
A
Gervais
Department of Chemistry, Center for Molecular Discovery (BU-CMD), Boston University , 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.
Kiel E
KE
Lazarski
Department of Chemistry, Center for Molecular Discovery (BU-CMD), Boston University , 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.
John A
JA
Porco
D001688:Biological Products; D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000737:chemistry*; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel; D013237:Stereoisomerism
D001688:Biological Products; D005663:Furans; D006575:Heterocyclic Compounds, 3-Ring; D007659:Ketones; C000605825:rhodomyrtosone A; C000605826:rhodomyrtosone B; D009532:Nickel; C039281:furan