Synthesis of an Ellagitannin Component, the Macaranoyl Group with a Tetra-ortho-Substituted Diaryl Ether Structure

Autor: Hashimoto, Hajime, Ishimoto, Takayuki, Konishi, Hayato, Hirokane, Tsukasa, Wakamori, Shinnosuke, Ikeuchi, Kazutada, Yamada, Hidetoshi
Jazyk: angličtina
Rok vydání: 2020
Zdroj: Organic letters. 22(17):6729-6733
ISSN: 1523-7060
Popis: Herein, a practical synthesis of the macaranoyl group contained in ellagitannins, i.e., a C-O digallate structure with a tetra-ortho-substituted diaryl ether bond, is described. The methodology involved an oxa-Michael addition/elimination reaction between a brominated ortho-quinone monoketal and a phenol with a hexahydroxydiphenoyl moiety in the presence of 18-crown-6 under dark conditions, followed by reductive aromatization. The existence of rotamers originating from the constructed ether moiety is discussed as well.
Databáze: OpenAIRE