Synthesis of 10-, 11- and 12-membered chiral benzolactones fused to furanose/pyranose sugars has been achieved in good to excellent yields using an intramolecular Sonogashira reaction. Positions 1–2, 3–5, 3–6 and 5–6 of sugar were utilized for the construction of the macrocycles. The requisite furanose/pyranose scaffolds were synthesized utilising conventional protection–deprotection strategies like benzylation, tritylation, detritylation, EDC coupling, propargylation, etc.