Total Synthesis of Terpioside B
Kazuki Inaba, Masato Endo, Naoto Iibuchi, Daisuke Takahashi, Kazunobu Toshima
Abstract
The first total synthesis of terpioside B (1) has been accomplished. Key steps include the stereoselective installments of a set of challenging 1,2-cis-glycosidic linkages. Thus, α(1,4)-linked d-galactoside was effectively constructed from a 1,2-anhydrogalactose donor and an unprotected 1,6-anhydrogalactose acceptor by using a boron-mediated aglycon delivery (BMAD) method. In addition, α-l-fucofuranosides were stereoselectively and simultaneously constructed by remote group-assisted 1,2-cis-α-stereoselective glycosylations.
Topics & Concepts
StereoselectivityTotal synthesisStereochemistryGlycosidic bondChemistryOrganic chemistryCatalysisEnzymeCarbohydrate Chemistry and SynthesisGlycosylation and Glycoproteins ResearchGenomics and Phylogenetic Studies