Myricanol 1, a constituent of Myrica species, has been reported to lower the levels of the microtubuleassociated 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.
Convergent total synthesis of (±) myricanol, a cyclic natural diarylheptanoid / Bochicchio, A.; Schiavo, L.; Chiummiento, L.; Lupattelli, P.; Funicello, M.; Hanquet, G.; Choppin, S.; Francoise, Colobert. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0539. - 16:(2018), pp. 8859-8869. [10.1039/c8ob02052c]
Convergent total synthesis of (±) myricanol, a cyclic natural diarylheptanoid
P. Lupattelli;
2018
Abstract
Myricanol 1, a constituent of Myrica species, has been reported to lower the levels of the microtubuleassociated 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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
