Synthesis and X-ray diffraction analysis of coenzyme Q derivatives obtained from natural polyalkoxyallylbenzenes

A general synthetic access to methoxy analogues of coenzymes Q bearing functional substituents with various chain lengths at the quinone ring was developed using available natural (polymethoxy)(methylenedioxy)allylbenzenes. The Baeyer–Villiger rearrangement of (methylenedioxy)benzaldehydes into phenols followed by facile oxidation to quinones with the methylenedioxy moiety opening was identified as the key step in the synthesis of the target 1,4- and 1,2-polyalkoxyquinones