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CuBr(2)-Catalyzed Mild Oxidation of 3,4-Dihydro-β-Carbolines and Application in Total Synthesis of 6-Hydroxymetatacarboline D
[Image: see text] A green chemical method for the conversion of 3,4-dihydro-β-carbolines to β-carbolines has been developed using air as the oxidant. With 15 mol % CuBr(2) as the catalyst, 3,4-dihydro-β-carbolines could be efficiently oxidized to β-carbolines in dimethyl sulfoxide at room temperatur...
| Autores principales: | , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical Society
2018
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6641302/ https://www.ncbi.nlm.nih.gov/pubmed/31457912 http://dx.doi.org/10.1021/acsomega.7b01908 |
| _version_ | 1783436749776617472 |
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| author | Meng, Tian-Zhuo Zheng, Jie Trieu, Tien Ha Zheng, Bo Wu, Jia-Jia Zhang, Yi Shi, Xiao-Xin |
| author_facet | Meng, Tian-Zhuo Zheng, Jie Trieu, Tien Ha Zheng, Bo Wu, Jia-Jia Zhang, Yi Shi, Xiao-Xin |
| author_sort | Meng, Tian-Zhuo |
| collection | PubMed |
| description | [Image: see text] A green chemical method for the conversion of 3,4-dihydro-β-carbolines to β-carbolines has been developed using air as the oxidant. With 15 mol % CuBr(2) as the catalyst, 3,4-dihydro-β-carbolines could be efficiently oxidized to β-carbolines in dimethyl sulfoxide at room temperature in the presence of 1,8-diazabicyclo[5,4,0]undec-7-ene (or Et(3)N). By applying this method, the first total synthesis of 6-hydroxymetatacarboline D was performed through 12 steps in 22% overall yield starting from l-5-hydroxy-tryptophan. |
| format | Online Article Text |
| id | pubmed-6641302 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2018 |
| publisher | American Chemical Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-66413022019-08-27 CuBr(2)-Catalyzed Mild Oxidation of 3,4-Dihydro-β-Carbolines and Application in Total Synthesis of 6-Hydroxymetatacarboline D Meng, Tian-Zhuo Zheng, Jie Trieu, Tien Ha Zheng, Bo Wu, Jia-Jia Zhang, Yi Shi, Xiao-Xin ACS Omega [Image: see text] A green chemical method for the conversion of 3,4-dihydro-β-carbolines to β-carbolines has been developed using air as the oxidant. With 15 mol % CuBr(2) as the catalyst, 3,4-dihydro-β-carbolines could be efficiently oxidized to β-carbolines in dimethyl sulfoxide at room temperature in the presence of 1,8-diazabicyclo[5,4,0]undec-7-ene (or Et(3)N). By applying this method, the first total synthesis of 6-hydroxymetatacarboline D was performed through 12 steps in 22% overall yield starting from l-5-hydroxy-tryptophan. American Chemical Society 2018-01-17 /pmc/articles/PMC6641302/ /pubmed/31457912 http://dx.doi.org/10.1021/acsomega.7b01908 Text en Copyright © 2018 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
| spellingShingle | Meng, Tian-Zhuo Zheng, Jie Trieu, Tien Ha Zheng, Bo Wu, Jia-Jia Zhang, Yi Shi, Xiao-Xin CuBr(2)-Catalyzed Mild Oxidation of 3,4-Dihydro-β-Carbolines and Application in Total Synthesis of 6-Hydroxymetatacarboline D |
| title | CuBr(2)-Catalyzed Mild Oxidation of
3,4-Dihydro-β-Carbolines and Application in Total Synthesis
of 6-Hydroxymetatacarboline D |
| title_full | CuBr(2)-Catalyzed Mild Oxidation of
3,4-Dihydro-β-Carbolines and Application in Total Synthesis
of 6-Hydroxymetatacarboline D |
| title_fullStr | CuBr(2)-Catalyzed Mild Oxidation of
3,4-Dihydro-β-Carbolines and Application in Total Synthesis
of 6-Hydroxymetatacarboline D |
| title_full_unstemmed | CuBr(2)-Catalyzed Mild Oxidation of
3,4-Dihydro-β-Carbolines and Application in Total Synthesis
of 6-Hydroxymetatacarboline D |
| title_short | CuBr(2)-Catalyzed Mild Oxidation of
3,4-Dihydro-β-Carbolines and Application in Total Synthesis
of 6-Hydroxymetatacarboline D |
| title_sort | cubr(2)-catalyzed mild oxidation of
3,4-dihydro-β-carbolines and application in total synthesis
of 6-hydroxymetatacarboline d |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6641302/ https://www.ncbi.nlm.nih.gov/pubmed/31457912 http://dx.doi.org/10.1021/acsomega.7b01908 |
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