Publications by authors named "Nai-Li Fan"
We report the first total synthesis of scleropentaside D, a unique -glycosidic ellagitannin, from the ketal derivative of scleropentaside A employing site-selective O4-protection of -acyl glycoside and copper-catalyzed oxidative coupling reaction of galloyl groups as the key steps. Our study confirms the proposed structure of this natural product, scleropentaside D, and demonstrates its effectiveness as an inhibitor of α-glycosidase.
View Article and Find Full Text PDFRecent development in the synthesis of C-glycosides involving glycosyl radicals.
Org Biomol Chem
July 2020
Article Synopsis
- C-Glycosylation using glycosyl radical intermediates is crucial for creating C-glycosides, which are vital components in many natural products and drugs.
- This review highlights advancements in C-glycoside synthesis from 1999 to 2020, focusing on stereoselectivity and innovative methods like α-alkoxyacyl telluride techniques, photo-mediated reactions, and transition-metal catalysis.
- It also covers metal-mediated reductive cross coupling and outlines unique strategies for achieving β-stereoselective C-glycosylation, including brief mentions of organotin-based methods.
With glycosyl ortho-alkynylbenzoates as donors, the highly efficient glycosylation of flavonoid 5-OH which are notorious for their low reactivity due to their involvement in the formation of strong intramolecular H-bonds was achieved under the catalysis of a Au(i) complex. Thus, a series of flavonoid 5-O-glycosides, including a kaempferol 5-O-disaccharide, were synthesized with good to excellent yields.
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