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A convenient short synthesis of 7-oxo-PGI2

✍ Scribed by István Tömösközi; Károly Kánai; Péter Győry; Gábor Kovács

Book ID
104220528
Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
207 KB
Volume
23
Category
Article
ISSN
0040-4039

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✦ Synopsis

In a resent paper' our group published the synthesis of 7-oxo-PG12(&) anewand stable proetaoyclin mimic with wneiderable biologioal activity. In this communication we wish to report a wnaiderably improved version elaborated for the eimple and effeotive preparation of this substance starting from the readily available* 11,15=diaoetyl-A6--PGI1 methyl eeter(a . Ssleotive hydroxylation of the enol ether double bond vith oate.lytio amount of osmium tetroxlde and 1.10lo2 equivalenta of tertiary K-oxide (a. g. K-methylmorpholine-K-oxide3 or trimethylamine-K-oxide) prooeeded emoothly in tetrahydrofurane wntaining l% water at room temperature affordingJa(80Eb)whioh maa subsequently wnverted to the isomerio methyl ketale & (methanol, catalytic boron trifluoride

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Stereocontrolled synthesis of 7-hydroxy-
Stereocontrolled synthesis of 7-hydroxy- and 7-acetoxy-PGI2: New stable PGI2 analogues
✍ Kiyoshi Bannai; Takeshi Toru; Takeo Ba; Toshio Tanaka; Noriaki Okamura; Kenzo Wa 📂 Article 📅 1981 🏛 Elsevier Science 🌐 French ⚖ 238 KB

Stable analogues of PGIz, 7-hydroxy-and 7-acetoxy-PGIz, were synthesized from protected PGIz methyl ester G via sulfoxides 6a, 6& through stereocontrolled sulfoxide-sulfenate rearrangement.