CuBr2-Catalyzed Mild Oxidation of 3,4-Dihydro-β-Carbolines and Application in Total Synthesis of 6-Hydroxymetatacarboline D | Zendy

TianZhuo Meng | Zendy; Jie Zheng | Zendy; Tien Ha Trieu | Zendy; Bo Zheng | Zendy; Jiajia Wu | Zendy; Yi Zhang | Zendy; XiaoXin Shi | Zendy

Open Access

CuBr₂-Catalyzed Mild Oxidation of 3,4-Dihydro-β-Carbolines and Application in Total Synthesis of 6-Hydroxymetatacarboline D

Author(s) -

TianZhuo Meng,

Jie Zheng,

Tien Ha Trieu,

Bo Zheng,

Jiajia Wu,

Yi Zhang,

XiaoXin Shi

Publication year - 2018

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.7b01908

Subject(s) - yield (engineering) , catalysis , dimethyl sulfoxide , chemistry , tryptophan , total synthesis , sulfoxide , nuclear chemistry , organic chemistry , medicinal chemistry , materials science , biochemistry , amino acid , metallurgy

A green chemical method for the conversion of 3,4-dihydro-β-carbolines to β-carbolines has been developed using air as the oxidant. With 15 mol % CuBr 2 as the catalyst, 3,4-dihydro-β-carbolines could be efficiently oxidized to β-carbolines in dimethyl sulfoxide at room temperature in the presence of 1,8-diazabicyclo[5,4,0]undec-7-ene (or Et 3 N). By applying this method, the first total synthesis of 6-hydroxymetatacarboline D was performed through 12 steps in 22% overall yield starting from l-5-hydroxy-tryptophan.

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