原创力文档synthesis of seco-chlorinated derivatives of phenanthroindolizidine precursors via friedel-crafts reactionphenanthroindolizidine seco-chlorinated衍生品的合成前体通过傅克反应.pdfVIP
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synthesis of seco-chlorinated derivatives of phenanthroindolizidine precursors via friedel-crafts reactionphenanthroindolizidine seco-chlorinated衍生品的合成前体通过傅克反应
Molecules 2010, 15, 8501-8506; doi:10.3390/molecule
OPEN ACCESS
molecules
ISSN 1420-3049
/journal/molecules
Communication
Synthesis of Seco-Chlorinated Derivatives of
Phenanthroindolizidine Precursors via Friedel-Crafts Reaction
Songtao Li, Li Han, Jiang Liu, Yihan Hu, Dan Zheng, Yingbo Fu and Xueshi Huang *
Department of Natural Products Chemistry, Pharmaceutical School, China Medical University,
Shenyang 110001, China
* Author to whom correspondence should be addressed; E-Mail: xshuang@;
Tel.: +00-86245250.
Received: 9 October 2010; in revised form: 14 November 2010 / Accepted: 14 November 2010 /
Published: 22 November 2010
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.
Keywords: phenanthroindolizidine; antitumor; Friedel-Crafts reaction
1. Introduction
Phenanthroindolizidine alkaloids, which were mainly isolated from Asclepiadaceae family [1], have
attracted an intense attention because of their notable biological properties [2], especially the antitumor
activity [3]. Many iso
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