Synthesis of seco-chlorinated derivatives of phenanthroindolizidine precursors via Friedel-Crafts reaction

Songtao Li; Li Han; Jiang Liu; Yihan Hu; Dan Zheng; Yingbo Fu; Xueshi Huang

doi:10.3390/molecules15118501

Synthesis of seco-chlorinated derivatives of phenanthroindolizidine precursors via Friedel-Crafts reaction

Molecules. 2010 Nov 22;15(11):8501-6. doi: 10.3390/molecules15118501.

Authors

Songtao Li¹, Li Han, Jiang Liu, Yihan Hu, Dan Zheng, Yingbo Fu, Xueshi Huang

Affiliation

¹ Department of Natural Products Chemistry, Pharmaceutical School, China Medical University, Shenyang 110001, China.

Abstract

In the course of synthesizing 3-demethyltylophorine (1) by Lewis acid catalyzed intramolecular Friedel-Crafts reaction starting from N-(3-hydroxy-2,6,7-trimethoxy-phenanthr-9-ylmethyl)-2-chloromethylpyrrolidine, two chlorinated phenanthrene derivatives N-(4,10-dichloro-3-hydroxy-2,6,7-trimethoxyphenanthr-9-ylmethyl)-2-chloromethylpyrrolidine (4) and N-(4-chloro-3-hydroxy-2,6,7-trimethoxyphenanthr-9-ylmethyl)-2-chloromethylpyrrolidine (5) were obtained. The structures of these compounds were determined by spectroscopic analysis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / chemistry*
Indolizines / chemical synthesis*
Indolizines / chemistry*
Magnetic Resonance Spectroscopy
Molecular Structure
Phenanthrolines / chemical synthesis*
Phenanthrolines / chemistry*
Stereoisomerism

Substances

Antineoplastic Agents
Indolizines
Phenanthrolines
phenanthroindolizidine