Lead tetraacetate oxidation of the Diels-Alder adduct of 7-dehydrocholestryl acetate with maleic anhydride | Zendy

L. BondarenkoGheorghiu | Zendy; Ljubinka Lorenc | Zendy; Mihailo Lj. Mihailovi | Zendy

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Lead tetraacetate oxidation of the Diels-Alder adduct of 7-dehydrocholestryl acetate with maleic anhydride

Author(s) -

L. BondarenkoGheorghiu,

Ljubinka Lorenc,

Mihailo Lj. Mihailovi

Publication year - 2000

Publication title -

journal of the serbian chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.227

H-Index - 45

eISSN - 1820-7421

pISSN - 0352-5139

DOI - 10.2298/jsc0003147b

Subject(s) - maleic anhydride , adduct , yield (engineering) , chemistry , pyridine , cycloaddition , medicinal chemistry , organic chemistry , double bond , polymer chemistry , catalysis , materials science , copolymer , metallurgy , polymer

The Diels-Alder adduct (3), obtained by cycloaddition of 7-dehydrocholesteryl acetate (1) and maleic anhydride (2), was heated at ca. 90 o C 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 ∆-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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