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Biosynthesis of terpenes and steroids. Part V. The synthesis of ergosta-5, 7, 22, 24 (28)-tetraen-3β-ol, a biosynthetic precursor of ergosterol

DHR Barton, T Shioiri, DA Widdowson

文献索引:Barton,D.H.R. et al. Journal of the Chemical Society [Section] C: Organic, 1971 , p. 1968 - 1974

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被引用次数: 43

摘要

The Diels–Alder adduct between ergosterol and 4-phenyl-1, 2, 4-triazolin-3, 5-dione is reconverted into ergosterol in high yield by reduction with lithium aluminium hydride. The adduct has been used in a synthesis of ergosta-5, 7, 22, 24 (28)-tetraen-3β-ol. An analogous synthesis of ergosta-5, 7, 22, 24 (28)-tetraen-3β-ol using radioactive intermediates enabled the intermediacy of this compound in ergosterol biosynthesis in yeast to be demonstrated.