Alkylation of a phytosterol precursor to give cyclolaudenol and 31-norcyclolaudenol involves retention of a hydrogen atom at C-24, elimination of a proton from the terminal methyl group arising from C-3′ of mevalonic acid, and probable retention of all three hydrogen atoms of the incoming methyl group of methionine.
E. L. Ghisalberti, N. J. de Souza, H. H. Rees, L. J. Goad and T. W. Goodwin, J. Chem. Soc. D, 1969, 1401 DOI: 10.1039/C29690001401
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