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

Organic & Biomolecular Chemistry Pub Date: 2018-11-02 DOI: 10.1039/C8OB02052C

Abstract

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.

Graphical abstract: Convergent total synthesis of (±) myricanol, a cyclic natural diarylheptanoid
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