Litcius/Paper detail

The catalytic asymmetric dearomatization of tryptamine for accessing <i>meso</i>-contiguous quaternary carbon centers of oligomeric cyclotryptamine alkaloids: a formal synthesis of hodgkinsine B

Hongbo Wei, Guzhou Chen, Huanhuan Zou, Zhiqiang Zhou, Pan Lei, Jiahang Yan, Weiqing Xie

2021Organic Chemistry Frontiers16 citationsDOI

Abstract

Herein, we disclosed a catalytic asymmetric dearomatization (CADA) of tryptamine <italic>via</italic> tandem [4 + 2] cycloaddition/cyclization with <italic>o</italic>-azaxylylene <italic>in situ</italic> generated from functionalized 3-bromooxindole promoted by chiral <italic>N</italic>,<italic>N</italic>′-dioxide/Ni(BF<sub>4</sub>)<sub>2</sub>.

Topics & Concepts

ChemistryTryptamineCatalysisStereochemistryCycloadditionOrganic chemistryBiochemistryAlkaloids: synthesis and pharmacologyTraditional and Medicinal Uses of AnnonaceaeChemical synthesis and alkaloids
The catalytic asymmetric dearomatization of tryptamine for accessing <i>meso</i>-contiguous quaternary carbon centers of oligomeric cyclotryptamine alkaloids: a formal synthesis of hodgkinsine B | Litcius