Lead tetraacetate oxidation of the Diels-Alder adduct of 7-dehydrocholestryl acetate with maleic anhydride
Olovotetraacetatna oksidacija Dils-Adlerovog adukta 7-dehidro-holesteril-acetata sa anhidridom maleinske kiseline
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The Diels-Alder adduct (3), obtained by cycloaddition of 7-dehydrocholesteryl
acetate (1) and maleic anhydride (2), was heated at ca. 90 oC 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.
Dils-Alderov adukt 3, dobiven cikloadicijom 7-dehidroholesteril-acetata 1 i
anhidrida maleinske kiseline 2, oksidovan je velikim viškom olovotetraacetata u
piridinskom rastvoru na oko 90 ºC u toku 5h. Pod navedenim uslovima izvršena je
oksidativna laktonizacija jedinjenja 3 sa participacijom olefinske D6
-dvogube veze
pri čemu su dobivena dva izomerna monolaktonska derivata 9 i 10 (u ukupnm prinosu od
oko 6%) i bislaktonski proizvod 11 (u prinosu od oko 11,5%); pri tome je nepromenjen
polazni adukt izolovan u prinosu od »36%.
Keywords:
Diels-Alder adduct / cholesteryl acetate / maleic anhydride / oxidative mono- and bis-lactonizationSource:
Journal of the Serbian Chemical Society, 2000, 65, 3, 147-156Publisher:
- Belgrade : Serbian Chemical Society
Note:
- The authors are grateful to the Serbian Academy of Sciences and Arts, and the Ministry of Sciences and Technology of Serbia for financial support.
DOI: 10.2298/JSC0003147B
ISSN: 0352-5139; 1820-7421