- A Unified Strategy for the Syntheses of the Isoquinolinium Alkaloids Berberine, Coptisine, and Jatrorrhizine
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Total syntheses of the antibacterial alkaloids berberine, coptisine, and jatrorrhizine have been achieved in four steps through a unified route. The key step of this strategy is an efficient intramolecular Friedel-Crafts alkoxyalkylation which, following oxidation, establishes the isoquinolinium core of these natural products. Herein, the design and development of this synthetic strategy, which has enabled the shortest and most efficient syntheses of these alkaloids reported to date, is described.
- Mori-Quiroz, Luis M.,Hedrick, Sidnee L.,De Los Santos, Andrew R.,Clift, Michael D.
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supporting information
p. 4281 - 4284
(2018/07/29)
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- Berberine type alkaloid production (by machine translation)
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[Problem] to efficiently produce the alkaloid production-type alkaloid berberine berberine. 2, 6 - Di - tert - butyl -4 - methylpyridine [solution] trifluoromethanesulfonic anhydride with certain compound after the intramolecular cyclization reaction, after reduction, de-bromo, quinone oxidants including a step of the manufacturing method of an aromatic ring. Figure 1 [drawing] (by machine translation)
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- Rhizoma Coptidis alkali salt of the synthetic method and its use
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The invention discloses a synthetic method and application of coptisine halate; the synthetic method of the coptisine halate comprises the following steps: 1) using formic acid and phosphoric acid accounting for 0-10% of by volume of the formic acid as solvents, adding anhydrous copper sulfate, sodium chloride and oxalaldehyde for reflux and stirring for reaction; 2) adding N-(2, 3-methylenedioxy-N-benzyl)-beta-(3, 4-methylenedioxy phenyl) ethylamine into the reaction system, continuing reflux for reaction; 3) after the reaction is completed, washing the filter cake with water to remove reaction residues; and 4) putting the filter cake into a NaHCO3 solution, heating, stirring, filtering while the solution is hot, adding haloid acid into the filtrate, and cooling for crystallization. The method sharply improve the coptisine halate yield from 23.4% to more than 70.2%, the coptisine halate yield is far beyond the range of expected yield, and an unexpected technical effect is achieved. The coptisine halate prepared by the method can be used for preparing weight reducing medicines and cardiovascular disease preventing drugs.
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Paragraph 0023-0031; 0048-0058
(2019/02/04)
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- The new shortcut synthesis of 8-oxocoptisine
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8-Oxocoptisine 1, a natural protoberberine alkaloid, can be more easily achieved starting from readily available and inexpensive berberine hydrochlorate 2. The structure of the target compound 1 was confirmed by melting point, 1H NMR, IR, MS and elemental analysis.
- Cui, Xiang Juan,Lu, Ying Ying,Zhao, Min,Qian, Shan,Wu, Yong
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p. 1281 - 1282
(2011/10/08)
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- From protopines to berbines: Synthesis of 1-methoxystylopine and its N-metho salts from coulteropine
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The transformation of protopines into berbines under improved conditions has been used to synthesize 1-methoxystylopine. Coulteropine, the main alkaloid from Romneya coulteri, was used as the starting protopine to accomplish the stereocontrolled synthesis of both cis and trans N-methyl-1-methoxystylopinium salts. The results of ab initio calculations (B3LYP/6-31G**) which are consistent with experimental data, sustain the influence of the C-1 substituent on both the conformational equilibrium of berbines and the rate of N-methylation.
- Valpuesta, Maria,Diaz, Amelia,Torres, Gregorio,Suau, Rafael
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p. 5053 - 5059
(2007/10/03)
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