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

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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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Publication details

The article was received on 21 Aug 2018, accepted on 01 Nov 2018 and first published on 02 Nov 2018


Article type: Paper
DOI: 10.1039/C8OB02052C
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Convergent total synthesis of (±) myricanol, a cyclic natural diarylheptanoid

    A. Bochicchio, L. Schiavo, L. Chiummiento, P. Lupattelli, M. Funicello, G. Hanquet, S. Choppin and F. Colobert, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB02052C

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