A practical synthesis of nobiletin, a polymethoxylated citrus flavone, was accomplished by utilizing our novel flavone synthesis. Synthetic nobiletin was labelled by selective demethylation and rapid incorporation of (11)C atom. Positron emission tomography images successfully visualized the brain distribution, which may provide therapeutic benefits in the treatment of Alzheimer's disease.
We present a practical synthesis of the polymethoxylated citrus flavone nobiletin that is suitable for use on a hundred gram scale. Ready availability of this compound and its derivatives will aid detailed chemical-biological investigations of their biological activities, including activation of signaling via the cAMP-dependent protein kinase A/extracellular signal-related protein kinase/cAMP response element-binding protein pathway.
Sophoraflavanone H (1) is a polyphenol with a hybrid-type
structure containing 2,3-diaryl-2,3-dihydrobenzofuran and flavanone
ring moieties. This compound and related analogues are promising leads
for antimicrobial and antitumor drug development. Here we describe
a total synthesis of 1 and its diastereomer. The dihydrobenzofuran
and flavanone rings were constructed by a Rh-catalyzed asymmetric
C–H insertion reaction and selective oxy-Michael reaction.
The absolute configuration of 1 was established by X-ray
crystallographic analysis and CD spectral investigation of synthetic
derivatives.
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