Total Syntheses of Pyocyanin, Lavanducyanin, and Marinocyanins A and B

Total syntheses of pyocyanin, lavanducyanin, and marinocyanins A and B have been accomplished. The N-substituted phenazin-1-one skeleton, a common framework of these natural products, was constructed through the oxidative condensation of pyrogallol with N-substituted benzene-1,2-diamine under an oxy...

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Bibliographic Details
Published inOrganic letters Vol. 21; no. 18; pp. 7311 - 7314
Main Authors Kohatsu, Haruki, Kamo, Shogo, Tomoshige, Shusuke, Kuramochi, Kouji
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.09.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
STREPTOMYCES
PSEUDOMONAS-AERUGINOSA
BIOSYNTHESIS
WS-9659
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Summary:Total syntheses of pyocyanin, lavanducyanin, and marinocyanins A and B have been accomplished. The N-substituted phenazin-1-one skeleton, a common framework of these natural products, was constructed through the oxidative condensation of pyrogallol with N-substituted benzene-1,2-diamine under an oxygen atmosphere in a single step. Regioselective bromination with N-bromosuccinimide at the C-2 position of N-alkylated phenazin-1-ones afforded brominated natural products.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b02601