Issue 6, 1970

Investigations on the biosynthesis of steroids and terpenoids. Part II. Role of 24-methylene derivatives in the biosynthesis of steroids and terpenoids

Abstract

24,25-Dihydro-24-methylenelanosterol has been synthesised from lanosterol and investigated as a potential precursor of eburicoic acid and of ergosterol.

Two new sterols, 24,25-dihydro-4α-methyl-24-methylenezymosterol and 3β-hydroxy-4α-methylcholesta-8(14),24-diene have been isolated from yeast residues and their structures have been determined. The constitution of 24,25-dihydro-4α-methyl-24-methylenezymosterol has been confirmed by a partial synthesis from the more abundant 4α-methylzymosterol.

4α-Methylzymosterol, 24,25-dihydro-4α-methyl-24-methylenezymosterol and obtusifoliol have been shown to be incorporated into ergosterol in yeast cultures. 4,4-Dimethylergosterol is, however, not a precursor.

By a trapping experiment in which tritium-labelled squalene oxide and unlabelled 24,25-dihydro-24-methylene-lanosterol were used it has been shown that the latter is almost certainly not on the biogenetically preferred route from lanosterol to ergosterol.

Article information

Article type
Paper

J. Chem. Soc. C, 1970, 775-785

Investigations on the biosynthesis of steroids and terpenoids. Part II. Role of 24-methylene derivatives in the biosynthesis of steroids and terpenoids

D. H. R. Barton, D. M. Harrison, G. P. Moss and D. A. Widdowson, J. Chem. Soc. C, 1970, 775 DOI: 10.1039/J39700000775

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