Stereocontrolled Intramolecular Iron-mediated Diene/Vinyl Ether Cyclocoupling Reactions

Pearson, Anthony J.; Zhang, Sheng; Sun, Huikai

doi:10.1021/jo301721d

Cited by 4 publications

(1 citation statement)

References 18 publications

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“…Initial attempts at the decomplexation of the iron complex by employing reported conditions were not satisfying. Decomplexation of 22 or 23 either with iron(III) chloride 34 or with anhydrous trimethylamine N-oxide (TMANO) 34a, 35 in DMF at 70 °C did not furnish the desired products. Decomplexation of either the free phenol 22 or its acetate 23 was accomplished in 18% and 61% yield, respectively by a mild oxidation with 2.5 equivalents of ammonium cerium (IV) nitrate (CAN) 36 in acetone (Scheme 4).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Nororipavine and Noroxymorphone via N- and O-Demethylation of Iron Tricarbonyl Complex of Thebaine

et al. 2016

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Thebaine was converted into its iron tricarbonyl complex, which underwent successive N-and O-demethylation with BrCN and BBr 3 , respectively. Decomplexation of the iron tricarbonyl moiety was accomplished with ammonium cerium(IV) nitrate (CAN) and base-catalyzed hydrolysis furnished nororipavine. When excess CAN was used the methoxydiene unit was converted into its C-14 nitrate that on hydrogenation and further hydrolysis furnished noroxymorphone. Full experimental and spectral data are provided for all key compounds.

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Section: Methodsmentioning

confidence: 99%