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Updated: Jun 26, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Synthesis of chiral cyclohexanes and carbasugars by 6-exo-dig radical cyclisation reactions
Rajeev K Shrivastava1, Elise Maudru, Gurdial Singh
1Department of Chemistry, University of Sunderland, Sunderland, SR1 3SD, UK. Rajeev.Shrivastava@edgehill.ac.uk
Abstract:
Treatment of 5-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-ribose with lithium acetylides gave mixtures of syn- and anti-alkynols 2a-2c which were separated following protection as methoxymethyl ethers. These were converted to the corresponding iodides which underwent 6-exo-dig radical cyclisation to afford chiral cyclohexanes and carbasugars. Oxidation of the primary alcohols 6a-b gave the corresponding aldehydes which on treatment with Grignard reagents afforded a mixture of alcohols. The corresponding iodides underwent similar 6-exo-dig cyclisation to give fully functionalised cyclohexanes.
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