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

Haruki Kohatsu; Shogo Kamo; Shusuke Tomoshige; Kouji Kuramochi

doi:10.1021/acs.orglett.9b02601

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

Haruki Kohatsu, Shogo Kamo, Shusuke Tomoshige, Kouji Kuramochi

LIF - Molecular and Chemical Life Science

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	7311-7314
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	18
DOIs	https://doi.org/10.1021/acs.orglett.9b02601
Publication status	Published - 2019 Sept 20

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title = "Total Syntheses of Pyocyanin, Lavanducyanin, and Marinocyanins A and B",

abstract = "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.",

author = "Haruki Kohatsu and Shogo Kamo and Shusuke Tomoshige and Kouji Kuramochi",

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AU - Kohatsu, Haruki

AU - Kamo, Shogo

AU - Tomoshige, Shusuke

AU - Kuramochi, Kouji

PY - 2019/9/20

Y1 - 2019/9/20

N2 - 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.

AB - 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.

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ER -

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

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