First total syntheses of four natural bioactive glucosides

Abstract

The efficient total syntheses of four biologically interesting natural glucosides Ethylconiferin, Butylconiferin, 2’-Butoxyethylconiferin and Balajaponin B, have been achieved for the first time starting from commercially available Vanilline via concise reaction sequence of 8–10 steps with the overall yield of 26–41%. This work definitely laid the foundation for the further pharmacological study of this kind of natural compounds. Meanwhile, currently developed approach could be used as a general synthetic strategy for the syntheses of other monolignol glucosides and their derivatives, and provides an opportunity for further study of the structure-activity relationship of this kind of glucosides.

Graphical Abstract

Keywords:

• Balajaponin B
• 2’-Butoxyethylconiferin
• butylconiferin
• Ethylconiferin
• total synthesis

Additional information

Funding

This work was supported by the National Natural Science Foundation of China [82003619, 81803561, 21702022] and Sichuan Science and Technology Program [2018JY0222, 2020YJ0487].