686776-27-2Relevant academic research and scientific papers
Novel synthetic method of novel antitumor drug trabectedin intermediate
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Paragraph 0069-0071, (2020/08/22)
The invention discloses a novel synthetic method of a novel anti-tumor drug trabectedin intermediate, and the applicant of the invention finds that the trabectedin intermediate with high chiral puritycan be obtained through several steps of conventional conversion reactions starting from cheap and natural amino acid L-tyrosine derivatives, so that a novel synthetic method is developed. Accordingto the synthesis method, cheap natural amino acid L-tyrosine derivatives are taken as raw materials, benzyl protection is firstly carried out, then selective phenolic hydroxylation is carried out, benzyl protection is carried out, methylation reaction and borane reduction reaction are carried out, and finally debenzylation protection is carried out, so that the trabectedin intermediate with high chiral purity is obtained. The novel synthesis method of the novel anti-tumor drug trabectedin intermediate has the advantages of mild reaction temperature, simple operation, low synthesis cost, high product chiral purity and the like, and the whole synthesis process has a wide industrial scale application prospect and is more beneficial to industrial production.
A Scalable Total Synthesis of the Antitumor Agents Et-743 and Lurbinectedin
He, Weiming,Zhang, Zhigao,Ma, Dawei
supporting information, p. 3972 - 3975 (2019/02/24)
An efficient and scalable approach is described for the total synthesis of the marine natural product Et-743 and its derivative lubinectedin, which are valuable antitumor compounds. The method delivers 1.6 % overall yield in 26 total steps from Cbz-protected (S)-tyrosine. It features the use of a common advanced intermediate to create the right and left parts of these compounds, and a light-mediated remote C?H bond activation to assemble a benzo[1,3]dioxole-containing intermediate.
Preparation of natural product Trabectedin
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Paragraph 0183-0188, (2019/07/04)
The invention provides a preparation method of a natural product Trabectedin, particularly an Et-743 preparation method, wherein tyrosine is used as a starting substrate, synthesis can be completed through a 26-step reaction, the raw materials and the reagents used in the synthetic route are relatively easy to obtain, the reaction conditions are relatively mild, and the method is suitable for large-scale preparation.
Tetrahydroisoquinoline intermediate of compound preparation method
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, (2017/08/25)
The invention provides a tetrahydroisoquinoline compound with the following structural general formula I. The invention also provides application of the above tetrahydroisoquinoline compound as an intermediate for the preparation of tetrahydroisoquinoline alkaloid natural medicaments. The invention further provides a method for preparing the tetrahydroisoquinoline compound. The method uses a halogenated aromatic compound as a starting material, and conducts nucleophilic substitution, addition, hydroxy elimination and protecting group elimination reaction, thereby obtaining the tetrahydroisoquinoline compound with chiral amine.
Synthesis of an isomer of the renieramycin skeleton from L -tyrosine
Liu, Wei,Dong, Wen Fang,Liao, Xiang Wei,Guan, Bao He,Liu, Zhan Zhu
, p. 414 - 418 (2011/06/20)
A new approach that tried to obviate the use of bromine protection groups was studied to synthesize (-)-renieramycin G from L-tyrosine. It was found that the first intermolecular Pictet-Spengler reaction proceeded successfully to give the correct tetrahyd
Total synthesis of (-)-MY 336a from L-tyrosine
Liao, Xiang Wei,Dong, Wen Fang,Liu, Wei,Guan, Bao He,Liu, Zhan Zhu
experimental part, p. 50 - 53 (2010/05/03)
(Chemical Equation Presented) Using L-tyrosine as a chiral starting material, we developed an efficient synthetic route to (-)-MY 336a. A key step in the sequence is a highly regio- and diastereoselective intermolecular Pictet-Spengler cyclization reaction between amino alcohol and benzyloxyacetaldehyde.
A new approach to the synthesis of l-3-hydroxy-4-methoxy-5-methyl-phenylalanine derivatives from l-tyrosine
Chen, Ruijiao,Zhu, Deguang,Hu, Zuoqiang,Zheng, Zhiming,Chen, Xiaochuan
experimental part, p. 39 - 42 (2010/04/24)
A practical procedure to regioselectively install a methyl group and a phenolic hydroxyl group onto l-tyrosine was developed. By using this approach, protected l-3-hydroxy-4-methoxy-5-methyl-phenylalanine and l-3-hydroxy-4-methoxy-5-methyl-phenylalanol, which are utilized in efficient syntheses of the relevant tetrahydroisoquinoline alkaloids, were prepared conveniently with high yield.
Synthesis of L-3-hydroxy-4-methoxy-5-methylphenylalanol
Demoulin, Nicolas,Zhu, Jieping
experimental part, p. 466 - 468 (2009/08/09)
The L-3-hydroxy-4-methoxy-5-methylphenylalanol, a common subunit of ecteinascidin and safracin family alkaloids, was synthesized from L-tyrosine in eight steps with an overall yield of 50%. Georg Thieme Verlag Stuttgart.
Intermediate and process of preparation of ecteinascidin using such intermediate
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Page/Page column 17-18, (2008/06/13)
The present invention concerns an intermediate of the following formula I in which R1 and R2 represent independently of each other a C1-C12 alkyl group, a (C1-C12 alkoxy)carbonyl group, opt
Synthetic studies toward ecteinascidin 743
Chen, Xiaochuan,Chen, Jinchun,De Paolis, Michael,Zhu, Jieping
, p. 4397 - 4408 (2007/10/03)
An efficient synthesis of a fully functionalized tetracycle (A-B-C-H) 7 containing a 1,4-bridged 10-membered lactone was developed. Phenolic aldol condensation between 2-methylsesamol (15) and Garner's aldehyde provided the protected amino diol 16, which
