Simple Total Synthesis of Photodynamic Compound 5-Aminolevulinic Acid

Abstract

5-Aminolevulinic acid (5-ALA) was prepared from γ-butyrolactone via alcoholysis, oxidation, Henry reaction, oxidation and hydrogenation. Especially Henry reaction was carried out through a solvent-free procedure in the presence of alumina supported potassium fluoride, and then oxidation of the nitroalkanol was finished using wet alumina supported chromium(VI) oxide. The structures of all the com-pounds were confirmed by ¹H NMR, IR and MS spectra.

Key words: Henry reaction, 5-aminolevulinic acid, total synthe-sis, γ-butyrolactone, photodynamic compound

Cite this article

LIU Hai-Ling^1,2,3,JIANG Huan-Feng*^,1,WANG Yu-Gang^1,2,3,LIU Peng^1,2,3. Simple Total Synthesis of Photodynamic Compound 5-Aminolevulinic Acid[J]. Chin. J. Org. Chem., 2005, 25(11): 1431-1433.

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[1]	Donghang Shen, Xin Li, Shimeng Guo, Xin Xie, Fajun Nan. Design and Synthesis Studies of α-Methylene-γ-butyrolactones Antagonists of GPR52 [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3916-3929.
[2]	Zhiyu Hu, Guofang Jiang, Zhiqiang Zhu, Bozhen Gong, Zongbo Xie, Zhanggao Le. One-Pot Domino Henry-Friedel-Crafts Alkylation Reaction in Deep Eutectic Solvent [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 325-332.
[3]	Mao Pu, Yang Liangru, Xiao Yongmei, Yuan Jinwei, Mai Wenpeng, Gao Jie, Zhang Xinchi. Synthesis of Chiral Imidazole Amino Alcohols and Their Application in the Asymmetric Copper-Catalyzed Henry Reaction [J]. Chin. J. Org. Chem., 2019, 39(2): 443-448.
[4]	Wu Lili, Su Yingpeng, Chong Siying, Zhang Weigang, Huang Danfeng, Wang Kehu, Hu Yulai. Chiral Thiourea Catalyzed Asymmetric Henry Reaction: Construction of Stereogenic Center Bearing a CF₃ Group from 2,2,2-Trifluoroacetophenone Substrates [J]. Chin. J. Org. Chem., 2017, 37(4): 936-942.
[5]	Yu Fengli, Dou Youtao, Zhao Dongmei, Xie Congxia, Yu Shitao. Synthesis of γ-Butyrolactone from trans-Cinnamaldehyde and Methyl p-Formylbenzoate Catalyzed by Thermoregulated Thiazolium Chiral Ionic Liquid [J]. Chin. J. Org. Chem., 2014, 34(6): 1190-1195.
[6]	Zhao Dongwang, Wu Yuetong, Chen Tingting, Dai Liyi, Wang Yuanyuan. Efficient and Convenient Synthesis of Ionic Liquid Supported SBA-15 Mesoporous Srganosilica and Its Beneficial Applications in Henry Reaction [J]. Chin. J. Org. Chem., 2013, 33(08): 1791-1797.
[7]	Zhang Peng, He Jun, Wan Ningning, Zhang Weidong, Hui Yonghai, Xie Zhengfeng. Bis-thiocarbohydrazones Schiff Base Mn(II) Complex as a Catalyst for Henry Reaction [J]. Chin. J. Org. Chem., 2013, 33(08): 1834-1838.
[8]	Chi Pengli, Xie Cuiyue, Lin Jimao. A Novel Synthetic Method of 5-Aminolevulinic Acid Hydrochloride [J]. Chin. J. Org. Chem., 2013, 33(03): 640-642.
[9]	Xu Shanshan, Zhou Yuhan, Qu Jingping. Asymmetric Henry Reaction Catalyzed by CuOTf/NNN Tridentate Pincer Ligand [J]. Chin. J. Org. Chem., 2012, 32(06): 1131-1135.
[10]	YI Bing, ZHANG Yang, SHU Xiao-Ma, YANG Yan, DU Wen-Le, LIU Zhan-Peng. Study on Henry Reaction Catalyzed by Dendritic Amines [J]. Chin. J. Org. Chem., 2011, 31(06): 874-877.
[11]	GAO Shu-Tao, XI Guo-Hong, LI Ning, WANG Chun, MA Jing-Jun. Organocatalytic Asymmetric Henry Reactions [J]. Chin. J. Org. Chem., 2010, 30(12): 1811-1819.
[12]	CUI Yuan-Chen, ZHANG He-Feng, LI Run-Tao, LIU Yi, XU Chu. Asymmetric Henry Reaction Catalyzed by Chitosan and Its L-Proline Derivative [J]. Chin. J. Org. Chem., 2010, 30(05): 707-712.
[13]	GAN, Chang-Sheng*; PAN, Jian. Recent Advances in the Catalytic Asymmetric Henry Reaction [J]. Chin. J. Org. Chem., 2008, 28(07): 1193-1198.
[14]	WANG Ya-Jun,SHEN Zong-Xuan,ZHANG Ya-Wen*. Henry Reaction of α-Ketoesters and α-Ketoamides [J]. Chin. J. Org. Chem., 2006, 26(9): 1291-1294.
[15]	LIU, Quan-Zhong, GONG, Liu-Zhu, JIANG, Yao-Zhong. Study on the Reduction of (S)-Malic Acid and (S)-Aspartic Acid by ZnCl₂-KBH₄ [J]. Chinese Journal of Organic Chemistry, 2004, 24(6): 637-640.

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