26267-66-3Relevant academic research and scientific papers
Synthesis of an ellagitannin component, the macaranoyl group with a tetra-ortho-substituted diaryl ether structure
Hashimoto, Hajime,Ishimoto, Takayuki,Konishi, Hayato,Hirokane, Tsukasa,Wakamori, Shinnosuke,Ikeuchi, Kazutada,Yamada, Hidetoshi
, p. 6729 - 6733 (2020)
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.
