Total Synthesis of Chelerythrine

doi:10.7503/cjcu20130279

Chem. J. Chinese Universities ›› 2013, Vol. 34 ›› Issue (8): 1858.doi: 10.7503/cjcu20130279

• Organic Chemistry • Previous Articles Next Articles

Total Synthesis of Chelerythrine

HUANG Kang-Lun, XIE Long-Guan, LÜ Pei, GUO Cui, XU Xiao-Hua

State Key Laboratory of Elemento-organic Chemistry, Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China

Received:2013-03-26 Online:2013-08-10 Published:2013-07-19
Contact: LongGuan Xie E-mail:xielg@syn.nankai.edu.cn

Abstract

Abstract:

Chelerythrine is an isoquinoline alkaloid isolated from Herba Chelidonii that possess complex structure and remarkable activities. In this work, its total synthetic approach was investigated. Key meditate methyl 6-iodo-2,3-dimethoxybenzoate(7) was obtained in six steps with(6-bromo-2,3-dimethoxyphenyl)methanol(1) as starting material. The core structure was efficiently constructed by palladium-catalyzed tandem reaction in one step. At the same time, a proposed mechanism of palladium-catalyzed tandem reaction was suggested and the chelerythrine was synthesized in 10 steps with a total yield of 60.9%. All compounds were confirmed by IR, ¹H NMR, ¹³C NMR and high resolution mass spectrometer(HRMS).

Key words: Benzo[c]phenanthridine, Chelerythrine, Total synthesis

CLC Number:

O629.3

TrendMD:

HUANG Kang-Lun, XIE Long-Guan, LÜ Pei, GUO Cui, XU Xiao-Hua. Total Synthesis of Chelerythrine[J]. Chem. J. Chinese Universities, 2013, 34(8): 1858.

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Total Synthesis of Chelerythrine

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