Concise semisynthesis of novel phenazine-vitamin E hybrids via regioselective tocopheryl ortho-quinone formation

[Display omitted] •Concise semisynthetic route to phenazine-vitamin E hybrids.•IBX regio and chemoselective oxidation in vitamin E series.•Efficient IBX mediated tocopheryl ortho-quinone formation. A regioselective method for the semisynthesis of phenazine derivatives has been disclosed through an e...

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Bibliographic Details
Published in:Tetrahedron letters 2018-07, Vol.59 (27), p.2627-2630
Main Authors: Viault, Guillaume, Helesbeux, Jean-Jacques, Richomme, Pascal, Séraphin, Denis
Format: Article
Language:English
Subjects:
Life Sciences
Natural product
Phenazine
Quinone
Semisynthesis
Vitamin E
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Summary:[Display omitted] •Concise semisynthetic route to phenazine-vitamin E hybrids.•IBX regio and chemoselective oxidation in vitamin E series.•Efficient IBX mediated tocopheryl ortho-quinone formation. A regioselective method for the semisynthesis of phenazine derivatives has been disclosed through an efficient IBX mediated ortho-quinone formation from vitamin E derivatives. High chemo- and regio-selectivity was observed during the oxidation step and the corresponding 5,6-ortho-quinones could react with various phenylenediamines. Thus, this methodology proves its interest as a concise semisynthetic pathway to phenazine-vitamin E hybrids with moderate to good yields.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2018.05.011