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Convergent total synthesis of (±) myricanol, a cyclic natural diarylheptanoid†
L. Schiavo,L. Chiummiento,P. Lupattelli,M. Funicello,G. Hanquet,S. Choppin,F. Colobert
Organic & Biomolecular Chemistry Pub Date : 11/02/2018 00:00:00 , 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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