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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Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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%.
Ključne reči:
Diels-Alder adduct / cholesteryl acetate / maleic anhydride / oxidative mono- and bis-lactonizationIzvor:
Journal of the Serbian Chemical Society, 2000, 65, 3, 147-156Izdavač:
- Belgrade : Serbian Chemical Society
Napomena:
- 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
WoS: 000086052500001
Scopus: 2-s2.0-0034422910
Institucija/grupa
IHTMTY - JOUR AU - Bondarenko-Gheorghiu, Lidija AU - Lorenc, Ljubinka AU - Mihailović, Milhailo Lj. PY - 2000 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/3500 AB - 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. AB - 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%. PB - Belgrade : Serbian Chemical Society T2 - Journal of the Serbian Chemical Society T1 - Lead tetraacetate oxidation of the Diels-Alder adduct of 7-dehydrocholestryl acetate with maleic anhydride T1 - Olovotetraacetatna oksidacija Dils-Adlerovog adukta 7-dehidro-holesteril-acetata sa anhidridom maleinske kiseline VL - 65 IS - 3 SP - 147 EP - 156 DO - 10.2298/JSC0003147B ER -
@article{ author = "Bondarenko-Gheorghiu, Lidija and Lorenc, Ljubinka and Mihailović, Milhailo Lj.", year = "2000", abstract = "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%.", publisher = "Belgrade : Serbian Chemical Society", journal = "Journal of the Serbian Chemical Society", title = "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", volume = "65", number = "3", pages = "147-156", doi = "10.2298/JSC0003147B" }
Bondarenko-Gheorghiu, L., Lorenc, L.,& Mihailović, M. Lj.. (2000). Lead tetraacetate oxidation of the Diels-Alder adduct of 7-dehydrocholestryl acetate with maleic anhydride. in Journal of the Serbian Chemical Society Belgrade : Serbian Chemical Society., 65(3), 147-156. https://doi.org/10.2298/JSC0003147B
Bondarenko-Gheorghiu L, Lorenc L, Mihailović ML. Lead tetraacetate oxidation of the Diels-Alder adduct of 7-dehydrocholestryl acetate with maleic anhydride. in Journal of the Serbian Chemical Society. 2000;65(3):147-156. doi:10.2298/JSC0003147B .
Bondarenko-Gheorghiu, Lidija, Lorenc, Ljubinka, Mihailović, Milhailo Lj., "Lead tetraacetate oxidation of the Diels-Alder adduct of 7-dehydrocholestryl acetate with maleic anhydride" in Journal of the Serbian Chemical Society, 65, no. 3 (2000):147-156, https://doi.org/10.2298/JSC0003147B . .