Structural Modifications and Chiral Applications of Brucine

doi:10.6023/cjoc202004049

Abstract

The recent advances on the structural modifications and chiral applications of Brucine are reviewed. Brucine is a naturally occuring molecule with multiple functional groups and a complex stereochemical structure. Selective structural modification of brucine is challenging, and a variety of methods to achieve selective modifications at its specific site are available. The aryl moiety undergoes demethoxypentafluorophenylation, and the amide moiety undergoes the condensation with primary amine, deoxycyanation, deoxygenative reduction, and α-oximation. The tertiary amine moiety undergoes N-oxidation, formal carbene insertions of C-N or α-C-H bonds, three-component reactions with benzynes and phenols, N-amidation with nitrene, and N-alkylation with halogenated hydrocarbons. The C=C subunit undergoes dihydroxylation and hydrogenation, while the ether subunit undergoes hydrogenative cleavage. The modified structures have high potential medicinal values. As a chiral resolution reagent, brucine has been widely used in the resolution of racemic carboxylic acids, phosphoric or phosphonic acids, phenols, alcohols and some drugs. Additionally, brucine and its modified structures also find applications as chiral auxiliaries, chiral catalysts or chiral ligands in asymmetric synthesis and catalysis.

Key words: brucine, structural modification, chiral resolution, asymmetric synthesis

Cite this article

Dong Ziyang, Yang Zhanhui, Xu Jiaxi. Structural Modifications and Chiral Applications of Brucine[J]. Chinese Journal of Organic Chemistry, 2020, 40(12): 4101-4121.

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马钱子碱的结构修饰和手性应用