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...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
| Published: |
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 |
| Summary: | 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. |
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| ISSN: | 0352-5139 1820-7421 |