Journal of the Serbian Chemical Society 2000 Volume 65, Issue 3, Pages: 147-156
https://doi.org/10.2298/JSC0003147B
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Lead tetraacetate oxidation of the Diels-Alder adduct of 7-dehydrocholestryl acetate with maleic anhydride
Bondarenko-Gheorghiu Lidija G. (Faculty of Chemistry, Belgrade + Center for Chemistry ICTM, Belgrade)
Lorenc Ljubinka B. (Faculty of Chemistry, Belgrade + Center for Chemistry ICTM, Belgrade)
Mihailovi] Mihailo Lj. (Faculty of Chemistry, Belgrade + Center for Chemistry ICTM, Belgrade)
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.
Keywords: Diels-Alder adduct, cholesteryl acetate, maleic anhydride, oxidative mono-and bis-lactonization