Practical synthesis of methyl 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)-h eptanoate 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 cataly...

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Bibliographic Details
Published inJournal of Saudi Chemical Society Vol. 21; no. 5; pp. 587 - 592
Main Authors Yu, Chuanming, Li, Guizhou, Huang, Xing, Jiang, Xinpeng, Wang, Xueyan
Format Journal Article
LanguageEnglish
Published Riyadh, Saudi Arabia Saudi Chemical Society 2017
Subjects
التخليق الكيميائي
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Summary:The key intermediate of misoprostol, methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-h eptanoate 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
ISSN:1319-6103