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Total Synthesis of the Flavonoid Natural Product Houttuynoid A
Jie Jian1, Jilin Fan1, Hui Yang1
1Department of Medicinal Chemistry and Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy/Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University , Guangzhou 510632, People's Republic of China.
Abstract:
The first total synthesis of the antiviral flavonoid houttuynoid A (1) has been achieved from aryl ketone 6 and benzofuran aldehyde 5 in nine linear steps. The C6-C3-C6 structure of the flavonoid was synthesized by an I2-catalyzed oxa-Michael addition of a chalcone intermediate, generated by the Claisen-Schmidt condensation of 5 and 6. This work provides a method for the synthesis of houttuynoids and provides a reference for the synthesis of the remaining members of the houttuynoid family.
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