AI Article Synopsis
- Treatment of a specific sugar derivative with lithium acetylides produced a mixture of two types of alkynols that were later isolated and protected.
- These alkynols were converted into iodides that underwent a radical cyclization process to create chiral cyclohexanes and carbasugars.
- The primary alcohols generated from oxidation formed aldehydes that reacted with Grignard reagents to yield various alcohols and some underwent further cyclization to produce functionalized cyclohexanes.
Article 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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Source |
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2605619 | PMC |
| http://dx.doi.org/10.3762/bjoc.4.43 | DOI Listing |
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