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Citation: WANG Yuan-Xing, FANG Zhi-Jie, GAO Jun-Feng, WANG Yu, DING Lei, YIN Xiao-Jin, HAN Xue-Lian. Synthesis of Tylophorine From Veratraldehyde[J]. Chinese Journal of Applied Chemistry, ;2007, 24(2): 215-219. shu

Synthesis of Tylophorine From Veratraldehyde

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a College of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094;
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b Key Laboratory of Food Science of Ministry of Education, Nanchang University, Nanchang 330047;
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c Jiangsu Simcere Pharmaceutical Research Company LTD., Nanjing

Corresponding author: FANG Zhi-Jie,
Received Date: 19 March 2006
Available Online: 22 June 2006

The total synthesis of(s)-(+)-tylophorine,an anti-tumor active compound,was completed via eight-step reactions using veratraldehyde(1),3,4-dimethoxyphenylacetic acid(2) and(S)-L-proline(6),as raw materials.In the procedure,3,4-dimethoxy-trans-α-(3',4'-dimethoxyphenyl) phenylcinnamic acid(3) was synthesized by the reaction of veratraldehyde and 3,4-dimethoxyphenylacetic acid in the presence of acetic anhydride/Et₃N and then oxidative coupling reaction using VOF₃ to form 2,3,6,7-tetramethoxyphenanthrene-9-carboxylic acid(4) at 0℃.The intermediate(4) in quinoline derived 2,3,6,7-tetramethoxyphenanthrene (5) via decarboxylation catalyzed by anhydrous CuSO₄ at 230℃.The Friedel-Crafts reaction of the intermedi-ate(5) with(S)-N-(trifluoroacetyl) prolyl chloride(6b) formed(S)-N-(trifluoroacetyl) 2,3,6,7-tetrame-thoxy-9-prolyl-phenanthrene(7).After purification on a silica gel column,the carbonyl group of the interme-diate(7) was reduced by triethylsilane in presence of BF₃·Et₂O at room temperature,and then the detriflu-oroacetylation was followed.Finally,a ring-closing reaction with formaldehyde gave the target compound(10) in the presence of hydrochloric acid.The intermediates and target compounds were characterized by NMR and MS spectra.The synthetic conditions were mild,the total yield and the purity of the target compounds were 3.5% and 98.5%(HPLC),respectively.
- tylophorine,
- veratraldehyde,
- synthesis,
- antitumor
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