A highly diastereoselective approach leading to tetrahydrofuran unit of an unnatural (±)-6′-epi-varitriol starting from an in-house 5-oxabicyclo[2.1.1]hexane derivative is reported. The resultant anti-alcohol via diastereoselective reduction of a γ,δ-unsaturated ketone has been subjected to 5-exo-trig iodoyclization using iodine and subsequent hydrogenolysis which affords titled tetrahydrofuran derivative. The prepared acyclic unsaturated polyol is a six-carbon sugar analogue and hence a carbocycle to carbohydrate route has been demonstrated. © 2015, Scientific Publishers. All rights reserved.