Regio- and Stereoselective C-Glycosylation of Indoles Using o-[1-(p-MeO-Phenyl)vinyl]benzoates (PMPVB) as Glycosyl Donors under Brønsted Acid Catalysis

Abstract

The alkene-based o-[1-(p-MeO-phenyl)vinyl]benzoates (PMPVB) donors that can be remotely activated under catalytic Brønsted acidic conditions have been utilized to synthesize the C-linked indolyl glycosides in a regio- and stereoselective manner. The highly reactive glycosyl donors allow the usage of the poorly nucleophilic N-Boc and N-acetyl indole derivatives, leading to the indolyl glycosides in excellent yields and stereoselectivities. Also, conditions were developed for recycling the byproduct, which significantly improves the potential of these donors.

Recent Advances and Strategies towards Synthesis of Indolyl and Tryptophan‐C‐Glycoside Scaffolds

“…Kancharla research group [45] explored the utility of alkene‐based o ‐[1‐( p ‐MeO‐phenyl)vinyl] benzoates (PMPVB) glycosyl donors to perform the C ‐glycosylation in a regio‐ and stereoselective manner of substituted indoles using Bronsted acid as a catalyst (Scheme 6).…”

Cobalt’s Dual Role in Promoting C3-Glycosylation of Indoles: Unraveling Mechanistic Insights

“…Aside from 2-indolyl- C -deoxyglycosides, acting as important bioactive analogues, 3-indolyl- C -deoxyglycosides also could be of potential application prospect as sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes, which would be an attractive and active topic. However, access to 3-indolyl- C -deoxyglycosides has been considerably less explored, mainly relying on the properly functionalized glycosyl donors that need to be preinstalled . In light of this, pursuing an alternative catalytic C3-glycosylation of indoles with unfunctionalized glycals might be worthwhile and practical for developing synthetic methods.…”