Intramolecular Base-Free Sonogashira Reaction for the Synthesis of Benzannulated Chiral Macrocycles Embedded in Carbohydrate Templates.

A base-free, intramolecular Sonogashira reaction-based general approach has been established for the diversity-oriented synthesis (DOS) of fused bi- and tricyclic systems containing benzannulated, 10- to 13-membered chiral macrocycles embedded in carbohydrate templates. Macrocycles with different ring sizes have been prepared by pre-designing the chiral building blocks. Base-sensitive groups like acetyl and TBDPS survived the reaction conditions. [ABSTRACT FROM AUTHOR]