Journal
ACS CATALYSIS
Volume 6, Issue 5, Pages 2831-2835Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b00154
Keywords
flavin reductase; oxidative decarboxylation; picolinic acid derivatives; streptonigrin; streptonigrone
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Funding
- National Natural Science Foundation of China (NNSFC) [31425001, 31370082]
- MOE of China
- Leopoldina Fellowship Program (German National Academy of Sciences Leopoldina) [LPDS 2013-12]
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In the flavin-reductase-catalyzed reducing condition, a mild and efficient alpha-hydroxylation and decarboxylation procedure using natural flavins as a catalyst and atmospheric oxygen as an external oxidizing agent has been successfully developed and applied to the synthesis of streptonigrone from streptonigrin. This reaction was achieved not only with streptonigrin analogues but also with structurally diverse electron-rich picolinic acid derivatives. The hydroxylation and decarboxylation may take place in a concerted manner.
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