Synthesis of both enantiomers of the meta,meta-bridged diarylheptanoid Myricanol

The meta,meta-bridged diarylheptanoid myricanol isolated from the stem bark of Myrica cerifera is able to lower the levels of tau protein – a protein involved in the progression of Alzheimer's disease and several other neurodegenerative diseases. This biological activity, however, is highly dependent upon the stereochemistry of the sample. Here we report the synthesis of both enantiomers of myricanol. Pivotal to the success of this approach is the use of a remote stereocenter to influence the axial chirality of an aryl-aryl bond formed through an intramolecular Suzuki-Miyaura reaction.