Affiliation:
1. Faculty of Life Sciences Tokyo University of Agriculture 1-1-1 Sakuragaoka, Setagaya-ku Tokyo 156-8502 Japan
2. School of Science Kwansei Gakuin University 1 Gakuen-Uegahara, Sanda Hyogo 669-1330 Japan
Abstract
AbstractStachyurin and casuarinin are ellagitannins, a class of polyphenols that exhibit various biological activities that have an impact on human health. Casuarinin is a stachyurin stereoisomer. These compounds contain the characteristic C‐glycosidic bond between the open‐chain d‐glucose and the phenol aromatic ring. Therefore, chemical elucidation of the C‐glycosidic bond reactivity is required to exploit their multiple bioactivities. This study developed a method for the divergent synthesis of stachyurin and casuarinin via the α‐selective C‐glycosylation as well as the β‐selective introduction of the oxygen functional group, focusing on structural specificity. The proposed method applies to the syntheses of stachyurin and casuarinin analogues, thereby facilitating the utilisation of their beneficial bioactivities.
Funder
Kato Memorial Bioscience Foundation
Subject
General Chemistry,Catalysis,Organic Chemistry