Practical synthesis of methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-heptanoate
The key intermediate of misoprostol, methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-heptanoate was prepared from commercially available suberic acid in 40% yield over five steps. The key step involved a ZnCl2 catalyzed Friedel-Crafts reaction between furan and 2,9-oxonanedione. Sulfuric acid catalyze...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2017-07-01
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| Series: | Journal of Saudi Chemical Society |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1319610317300248 |
| _version_ | 1819056691036028928 |
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| author | Xinpeng Jiang Xueyan Wang Xing Huang Guizhou Li Chuanming Yu |
| author_facet | Xinpeng Jiang Xueyan Wang Xing Huang Guizhou Li Chuanming Yu |
| author_sort | Xinpeng Jiang |
| collection | DOAJ |
| description | The key intermediate of misoprostol, methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-heptanoate was prepared from commercially available suberic acid in 40% yield over five steps. The key step involved a ZnCl2 catalyzed Friedel-Crafts reaction between furan and 2,9-oxonanedione. Sulfuric acid catalyzed methylation of 8-(furan-2-yl)-8-oxooctanoic acid followed by sequential reduction and ZnCl2 catalyzed Piancatelli rearrangement resulted in the formation of the key intermediate of misoprostol. |
| first_indexed | 2024-12-21T13:27:26Z |
| format | Article |
| id | doaj.art-1478ef1a846c4ddcb4d13ea36b499b20 |
| institution | Directory Open Access Journal |
| issn | 1319-6103 |
| language | English |
| last_indexed | 2024-12-21T13:27:26Z |
| publishDate | 2017-07-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Saudi Chemical Society |
| spelling | doaj.art-1478ef1a846c4ddcb4d13ea36b499b202022-12-21T19:02:24ZengElsevierJournal of Saudi Chemical Society1319-61032017-07-0121558759210.1016/j.jscs.2017.01.004Practical synthesis of methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-heptanoateXinpeng Jiang0Xueyan Wang1Xing Huang2Guizhou Li3Chuanming Yu4College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, PR ChinaCollaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, PR ChinaCollaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, PR ChinaCollaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, PR ChinaCollege of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, PR ChinaThe key intermediate of misoprostol, methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-heptanoate was prepared from commercially available suberic acid in 40% yield over five steps. The key step involved a ZnCl2 catalyzed Friedel-Crafts reaction between furan and 2,9-oxonanedione. Sulfuric acid catalyzed methylation of 8-(furan-2-yl)-8-oxooctanoic acid followed by sequential reduction and ZnCl2 catalyzed Piancatelli rearrangement resulted in the formation of the key intermediate of misoprostol.http://www.sciencedirect.com/science/article/pii/S1319610317300248MisoprostolDehydrate cyclizationFriedel-Crafts acylationPiancatelli rearrangement |
| spellingShingle | Xinpeng Jiang Xueyan Wang Xing Huang Guizhou Li Chuanming Yu Practical synthesis of methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-heptanoate Journal of Saudi Chemical Society Misoprostol Dehydrate cyclization Friedel-Crafts acylation Piancatelli rearrangement |
| title | Practical synthesis of methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-heptanoate |
| title_full | Practical synthesis of methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-heptanoate |
| title_fullStr | Practical synthesis of methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-heptanoate |
| title_full_unstemmed | Practical synthesis of methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-heptanoate |
| title_short | Practical synthesis of methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-heptanoate |
| title_sort | practical synthesis of methyl 7 3 hydroxy 5 oxocyclopent 1 en 1 yl heptanoate |
| topic | Misoprostol Dehydrate cyclization Friedel-Crafts acylation Piancatelli rearrangement |
| url | http://www.sciencedirect.com/science/article/pii/S1319610317300248 |
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