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Diastereoselective synthesis of tetrahydrofuran unit of (±)-6′-epi-varitriol from 5-oxabicyclo[2.1.1]hexane derivative
S.H. Mahadevegowda,
Published in Scientific Publishers
2015
Volume: 54B
   
Issue: 8
Pages: 958 - 964
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. © 2015, Scientific Publishers. All rights reserved.
About the journal
JournalIndian Journal of Chemistry - Section B Organic and Medicinal Chemistry
PublisherScientific Publishers
ISSN03764699