Efficient synthesis of natural polyphenolic stilbenes: resveratrol, piceatannol and oxyresveratrol.
The practical synthesis of important natural polyphenolic stilbenes, including resveratrol, piceatannol and oxyresveratrol, through Perkin methodology is described. Starting from 3,5-dihydoxyacetophenone (1), the common intermediate 3,5-dimethoxyphenylacetic acid (3) can be obtained via methylation and Willgerodt-Kindler reaction. Perkin condensations between (3) and substituted phenylaldehydes 4 furnished E-2,3-diarylacrylic acids 5, followed by decarboxylation in Cu/quinoline giving stilbene intermediates 6 which bear the Z-configuration. Finally, through a simultaneous demethylation/isomerization process in AlI₃/CH₃CN system, the target compounds 7a-c can be obtained respectively in good to high overall yields. The synthetic method proved to be more concise, trans-specific, mild, economical and commonly applicable.
Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou, PR China.
Hong-Yi
HY
Sun
Chun-Fen
CF
Xiao
Yu-Chen
YC
Cai
Yu
Y
Chen
Wen
W
Wei
Xian-Ke
XK
Liu
Ze-Liang
ZL
Lv
Yong
Y
Zou
D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry; D045468:Fallopia japonica / Q000737:chemistry; D005419:Flavonoids / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D029586:Moraceae / Q000737:chemistry; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry; D010936:Plant Extracts / Q000138:chemical synthesis* / Q000737:chemistry; D010944:Plants / Q000737:chemistry*; D059808:Polyphenols; D011505:Protein-Tyrosine Kinases / Q000037:antagonists & inhibitors*; D000077185:Resveratrol; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry
D000972:Antineoplastic Agents, Phytogenic; D000975:Antioxidants; D005419:Flavonoids; D010636:Phenols; D010936:Plant Extracts; D059808:Polyphenols; D013267:Stilbenes; C034912:puag-haad; C041525:3,3',4,5'-tetrahydroxystilbene; D011505:Protein-Tyrosine Kinases; D000077185:Resveratrol