One-pot synthesis of trisubstituted monomethylated benzene-1,3-diols via a Michael addition-Dieckmann cyclization sequence from methyl (E)-3-methoxy-4-methoxycarbonylbut-2-enoate anion and methyl alkynoates and its application to the total synthesis

摘要

The reaction of methyl (E)-3-methoxy-4-methoxycarbonylbut-2-enoate (1) with a number of methyl alkynoates under appropriate conditions gave the monomethylated trisubstituted resorcinol derivatives 3 in a regiocontrolled manner, via a Michael addition-Dieckmann cyclization sequence in one pot. The resorcinol 3d, prepared in this manner, was used as the starting material for a three step, highly efficient (54% from 3d) synthesis of the bioactive fungal metabolite nidulol (4).