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Total Synthesis of the Flavonoid Natural Product Houttuynoid A

Author:
Jian, Jie, Fan, Jilin, Yang, Hui, Lan, Ping, Li, Manmei, Liu, Peijun, Gao, Hao, Sun, Pinghua
Source:
Journal of natural products 2018 v.81 no.2 pp. 371-377
ISSN:
1520-6025
Subject:
aldehydes, chalcone, condensation reactions
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.
Agid:
6043055