Diversity-Oriented Synthesis of Steviol Glycosides

作者:Qiao, Zhi; Liu, Hui; Sui, Jing-Jing; Liao, Jin-Xi; Tu, Yuan-Hong; Schmidt, Richard R.*; Sun, Jian-Song*
来源:Journal of Organic Chemistry, 2018, 83(19): 11480-11492.
DOI:10.1021/acs.joc.8b01274

摘要

With cheap and easily available mixtures of steviol glycosides as starting materials, a practical method for steviol acquisition has been developed, on the basis of which a facile, diversity-oriented, and economic protocol for the synthesis of structurally defined steviol glycosides was established. The novel approach is featured by the highly efficient glycosylation of sterically hindered and acid-sensitive steviol via orchestrated application of Yu glycosylation, Schmidt glycosylation, and PTC glycosylation. Hence, these high-intensity sweeteners and potential lead compounds for drug development are now readily accessible.