Diastereoselective synthesis of tetrahydrofuran unit of (±)-6′-epi-varitriol from 5-oxabicyclo[2.1.1]hexane derivative

Mahadevegowda, S H and Khan, Faiz Ahmed (2015) Diastereoselective synthesis of tetrahydrofuran unit of (±)-6′-epi-varitriol from 5-oxabicyclo[2.1.1]hexane derivative. Indian Journal of Chemistry : Section B, 54B. pp. 958-964. ISSN 0376-4699

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Abstract

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.

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