Reaction of methyl gibberellate with triphenylphosphine and carbon tetrachloride

Abstract

Treatment of methyl gibberellate and its 3-epimer with triphenylphosphine and carbon tetrachloride containing acetone or pyridine, gave the 1β-chloro- and 1β,13-dichloro-Δ²-derivatives respectively as the major products. The 3-chloro-compounds were obtained as minor products. The 1-bromo-compounds were obtained with carbon tetrabromide. The structures of these compounds were established by location of the label in the products from methyl 3-epi-[3β-²H]gibberellate.