The removal of C(20) in gibberellins
Abstract
Oxidative decarboxylation of ent-gibberellane-19,20-dioic acids with lead tetra-acetate yields mixtures of 19,10-lactones and 20,4-lactones providing a chemical correlation between the C20 and C19 gibberellins. The oxidation of methyl ent-16-oxo-17-norgibberell-2-ene-7,19,20-trioate with chromium trioxide afforded a 1-ketone which underwent decarboxylation with lithium iodide to afford a 20-norgibberellane with a transA–B ring fusion.