Synthesis of Deuterio-labelled 24-Methylenecholesterol and Related Steroids†

Abstract

[25,26,27-²H₇]24-Methylenecholesterol 2b, [26,27-²H₆]24-methyldesmosterol 3b, [25,26,27-²H₇]ergosta-4,24(28)-dien-3β-ol 4b, [25,26,27-²H₇]ergosta-4,24(28)-dien-3-one 5b, [25,26,27-²H₇]5α-ergost-24(28)-en-3-one 6b and [25,26,27-²H₇]5α-ergost-24(28)-en-3β-ol 7b are prepared from the known 3β-tetrahydropyranyloxychol-5-en-24-al 8; they are of use both as internal standards in quantitative analyses and as substrates for metabolic studies in brassinosteroid-deficient mutants of Arabidopsis thaliana and Pisum sativum.