Protecting group improvement by isotopic substitution: application to the synthesis of the quinone system of fredericamycin A

Abstract

Use of a trideuteriomethoxy group for phenol protection, instead of the classical methoxy group, serves to suppress an unwanted intramolecular hydrogen transfer during a radical cyclization experiment, and leads to a spiro compound of a type that can be converted into the spiro diketone–quinone system of the antitumour agent, fredericamycin A.