School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan.
Org Lett. 2020 May 1;22(9):3392-3396. doi: 10.1021/acs.orglett.0c00876. Epub 2020 Apr 10.
This study involves the total synthesis of casuarinin, a naturally occurring ellagitannin, in which an open-chain glucose is esterified with two ()-hexahydroxydiphenoyl (HHDP) groups. One HHDP group incorporates a C-glycosidic bond between its benzene ring and the glucose moiety, which was constructed with complete stereoselectivity using a benzyl oxime group that opened the glucopyranose ring and acted as a scaffold for C-glycoside production. This total synthesis enables future structure-activity relationship studies of this compound.
本研究涉及天然鞣花单宁 casuarinin 的全合成，其中一个开链葡萄糖与两个（）-六羟基二苯甲酰基（HHDP）酯化。一个 HHDP 基团在其苯环和葡萄糖部分之间形成 C-糖苷键，这是使用苯甲肟基团构建的，该基团打开葡萄糖环并作为 C-糖苷产物的支架，具有完全的立体选择性。该全合成能够为该化合物的未来结构-活性关系研究提供支持。
