Convergent total synthesis of (±) myricanol, a cyclic natural diarylheptanoid.

Org Biomol Chem

Department of Science, University of Basilicata, Via dell'Ateneo lucano, 10, 85100 Potenza, Italy.

Published: November 2018

Myricanol 1, a constituent of Myrica species, has been reported to lower the levels of the microtubule-associated protein tau (MAPT), whose accumulation plays an important role in some neurodegenerative diseases, such as Alzheimer's disease (AD). Herein we described a new synthetic route to prepare myricanol in 9 steps and 4.9% overall yield starting from commercially available 2,3-dimethoxyphenol and methyl 3-(4-benzyloxyphenyl)propanoate. The key steps are a cross-metathesis to obtain a linear diarylheptanoid intermediate and a Suzuki-Miyaura domino reaction to generate the challenging macrocycle.

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http://dx.doi.org/10.1039/c8ob02052cDOI Listing

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