Reaction of ergosteryl acetate with maleic anhydride and preparation of 5,7-ergostadien-3beta-ol1,2

Reaction of ergosteryl acetate with maleic anhydride and preparation of 5,7-ergostadien-3beta-ol1,2

An improved, large scale synthesis of the ergosteryl acetate-maleic anhydride Diels-Alder adduct and its pyrolysis are described. The complex mixture obtained by reaction of the two constituents was refluxed with methanol to convert the succinic anhydride derivatives, formed by the "ene" r...

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Veröffentlicht in:Lipids 1975-09, Vol.10 (9), p.517-523
Hauptverfasser: Kircher, H W, Rosenstein, F U
Format: Artikel
Sprache:eng
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Anhydrides
Chromatography, Thin Layer
Ergosterol - analogs & derivatives
Maleates
Methods
Spectrophotometry, Ultraviolet
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creator Kircher, H W
Rosenstein, F U
description An improved, large scale synthesis of the ergosteryl acetate-maleic anhydride Diels-Alder adduct and its pyrolysis are described. The complex mixture obtained by reaction of the two constituents was refluxed with methanol to convert the succinic anhydride derivatives, formed by the "ene" reaction, to soluble half esters, leaving the insoluble Diels-Alder adduct largely unchanged. The latter was hydrogenated and pyrolyzed in vacuo to yield 5,7-ergostadienyl acetate together with lesser quantities of the acetates of 7,9(11)-ergostadien-3beta-ol, 6,8(9)-ergostadien-3beta-ol, and 8,14-ergostadien-3beta-ol. These components were separated and purified by argentation column chromatography and crystallization.
doi_str_mv 10.1007/BF02532352
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source MEDLINE; Springer Nature - Complete Springer Journals
subjects Anhydrides
Chromatography, Thin Layer
Ergosterol - analogs & derivatives
Maleates
Methods
Spectrophotometry, Ultraviolet
title Reaction of ergosteryl acetate with maleic anhydride and preparation of 5,7-ergostadien-3beta-ol1,2
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