Lead tetraacetate oxidation of the Diels-Alder adduct of 7-dehydrocholestryl acetate with maleic anhydride
The Diels-Alder adduct (3), obtained by cycloaddition of 7-dehydrocholesteryl acetate (1) and maleic anhydride (2), was heated at ca. 90°C with a large excess of lead tetraacetate in pyridine solution for 5 h. Under these conditions, compound 3 underwent lactonization with the participation of the o...
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| Format: | Article |
| Language: | English |
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Serbian Chemical Society
2000-03-01
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| Series: | Journal of the Serbian Chemical Society |
| Subjects: | |
| Online Access: | http://www.shd.org.yu/HtDocs/SHD/Vol65/No3-Pdf/V65-No3-01.zip |
| _version_ | 1818209380961615872 |
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| author | MIHAILO LJ. MIHAILOVIC LJUBINKA B. LORENC LIDIJA G. BONDARENKO-GHEORGHIU |
| author_facet | MIHAILO LJ. MIHAILOVIC LJUBINKA B. LORENC LIDIJA G. BONDARENKO-GHEORGHIU |
| author_sort | MIHAILO LJ. MIHAILOVIC |
| collection | DOAJ |
| description | The Diels-Alder adduct (3), obtained by cycloaddition of 7-dehydrocholesteryl acetate (1) and maleic anhydride (2), was heated at ca. 90°C with a large excess of lead tetraacetate in pyridine solution for 5 h. Under these conditions, compound 3 underwent lactonization with the participation of the olefinic D6-double bond to give two isomeric monolactone derivatives, 9 and 10 (in a total yield of ca. 6%), and the bislactone product 11 (in 11.5% yield). The starting material was recovered in 36% yield. |
| first_indexed | 2024-12-12T04:59:48Z |
| format | Article |
| id | doaj.art-6b5904ce86194b27b3f66b05e66a7115 |
| institution | Directory Open Access Journal |
| issn | 0352-5139 |
| language | English |
| last_indexed | 2024-12-12T04:59:48Z |
| publishDate | 2000-03-01 |
| publisher | Serbian Chemical Society |
| record_format | Article |
| series | Journal of the Serbian Chemical Society |
| spelling | doaj.art-6b5904ce86194b27b3f66b05e66a71152022-12-22T00:37:16ZengSerbian Chemical SocietyJournal of the Serbian Chemical Society0352-51392000-03-01653147156Lead tetraacetate oxidation of the Diels-Alder adduct of 7-dehydrocholestryl acetate with maleic anhydrideMIHAILO LJ. MIHAILOVICLJUBINKA B. LORENCLIDIJA G. BONDARENKO-GHEORGHIUThe Diels-Alder adduct (3), obtained by cycloaddition of 7-dehydrocholesteryl acetate (1) and maleic anhydride (2), was heated at ca. 90°C with a large excess of lead tetraacetate in pyridine solution for 5 h. Under these conditions, compound 3 underwent lactonization with the participation of the olefinic D6-double bond to give two isomeric monolactone derivatives, 9 and 10 (in a total yield of ca. 6%), and the bislactone product 11 (in 11.5% yield). The starting material was recovered in 36% yield.http://www.shd.org.yu/HtDocs/SHD/Vol65/No3-Pdf/V65-No3-01.zipDiels-Alder adductcholesteryl acetatemaleic anhydrideoxidative mono- and bis-lactonization |
| spellingShingle | MIHAILO LJ. MIHAILOVIC LJUBINKA B. LORENC LIDIJA G. BONDARENKO-GHEORGHIU Lead tetraacetate oxidation of the Diels-Alder adduct of 7-dehydrocholestryl acetate with maleic anhydride Journal of the Serbian Chemical Society Diels-Alder adduct cholesteryl acetate maleic anhydride oxidative mono- and bis-lactonization |
| title | Lead tetraacetate oxidation of the Diels-Alder adduct of 7-dehydrocholestryl acetate with maleic anhydride |
| title_full | Lead tetraacetate oxidation of the Diels-Alder adduct of 7-dehydrocholestryl acetate with maleic anhydride |
| title_fullStr | Lead tetraacetate oxidation of the Diels-Alder adduct of 7-dehydrocholestryl acetate with maleic anhydride |
| title_full_unstemmed | Lead tetraacetate oxidation of the Diels-Alder adduct of 7-dehydrocholestryl acetate with maleic anhydride |
| title_short | Lead tetraacetate oxidation of the Diels-Alder adduct of 7-dehydrocholestryl acetate with maleic anhydride |
| title_sort | lead tetraacetate oxidation of the diels alder adduct of 7 dehydrocholestryl acetate with maleic anhydride |
| topic | Diels-Alder adduct cholesteryl acetate maleic anhydride oxidative mono- and bis-lactonization |
| url | http://www.shd.org.yu/HtDocs/SHD/Vol65/No3-Pdf/V65-No3-01.zip |
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