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. 90ºC with a large excess of lead tetraacetate in pyridine solution for 5h. Under these conditions, compound 3 underwent lactonization with the participation...
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| Format: | Article |
| Language: | English |
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Serbian Chemical Society
2000-01-01
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| Series: | Journal of the Serbian Chemical Society |
| Subjects: | |
| Online Access: | http://www.doiserbia.nb.rs/img/doi/0352-5139/2000/0352-51390003147B.pdf |
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| author | Bondarenko-Gheorghiu Lidija G. Lorenc Ljubinka B. Mihailovi] Mihailo Lj. |
| author_facet | Bondarenko-Gheorghiu Lidija G. Lorenc Ljubinka B. Mihailovi] Mihailo Lj. |
| author_sort | Bondarenko-Gheorghiu Lidija G. |
| collection | DOAJ |
| description | The Diels-Alder adduct (3), obtained by cycloaddition of 7-dehydrocholesteryl
acetate (1) and maleic anhydride (2), was heated at ca. 90ºC with a large
excess of lead tetraacetate in pyridine solution for 5h. Under these
conditions, compound 3 underwent lactonization with the participation of the
olefinic Δ6-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 | 2024-12-20T01:18:43Z |
| format | Article |
| id | doaj.art-439f2817d6304a43aec08fabcb34be5c |
| institution | Directory Open Access Journal |
| issn | 0352-5139 1820-7421 |
| language | English |
| last_indexed | 2024-12-20T01:18:43Z |
| publishDate | 2000-01-01 |
| publisher | Serbian Chemical Society |
| record_format | Article |
| series | Journal of the Serbian Chemical Society |
| spelling | doaj.art-439f2817d6304a43aec08fabcb34be5c2022-12-21T19:58:29ZengSerbian Chemical SocietyJournal of the Serbian Chemical Society0352-51391820-74212000-01-0165314715610.2298/JSC0003147B0352-51390003147BLead tetraacetate oxidation of the Diels-Alder adduct of 7-dehydrocholestryl acetate with maleic anhydrideBondarenko-Gheorghiu Lidija G.0Lorenc Ljubinka B.1Mihailovi] Mihailo Lj.2Faculty of Chemistry, Belgrade + Center for Chemistry ICTM, BelgradeFaculty of Chemistry, Belgrade + Center for Chemistry ICTM, BelgradeFaculty of Chemistry, Belgrade + Center for Chemistry ICTM, BelgradeThe Diels-Alder adduct (3), obtained by cycloaddition of 7-dehydrocholesteryl acetate (1) and maleic anhydride (2), was heated at ca. 90ºC with a large excess of lead tetraacetate in pyridine solution for 5h. Under these conditions, compound 3 underwent lactonization with the participation of the olefinic Δ6-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.doiserbia.nb.rs/img/doi/0352-5139/2000/0352-51390003147B.pdfdiels-alder adductcholesteryl acetatemaleic anhydrideoxidative mono-and bis-lactonization |
| spellingShingle | Bondarenko-Gheorghiu Lidija G. Lorenc Ljubinka B. Mihailovi] Mihailo Lj. 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.doiserbia.nb.rs/img/doi/0352-5139/2000/0352-51390003147B.pdf |
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