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 inTetrahedron letters Vol. 59; no. 27; pp. 2627 - 2630
Main Authors Viault, Guillaume, Helesbeux, Jean-Jacques, Richomme, Pascal, Séraphin, Denis
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 04.07.2018
Elsevier
Subjects
Chemistry
Chemistry, Organic
Life Sciences
Natural product
Phenazine
Physical Sciences
Quinone
Science & Technology
Semisynthesis
Vitamin E
Natural product
Phenazine
Semisynthesis
Vitamin E
Quinone
DESIGN
NATURAL-PRODUCTS
OXIDATION-PRODUCTS
MOLECULES
TOCOTRIENOLS
PHENOLS
BIOSYNTHESIS
LEADS
AGENTS
semisynthesis
phenazine
natural product
quinone
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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