Design and synthesis of carbohydrate based medium sized sulfur containing benzannulated macrocycles: applications of Sonogashira and Heck coupling

Palladium catalyzed intramolecular Sonogashira and Heck coupling reactions have been applied for diversity-oriented synthesis of sulfur containing carbohydrate based medium sized ring macrocycles. The process involves design and synthesis of building blocks with predisposed functional units prerequisite for C-C coupling. Both cis- and trans-fused benzannulated medium sized macrocyles with different ring sizes (8-13-membered) fused at different positions of furannose and pyranose moiety have been achieved.