Synthesis of chiral cyclohexanes and carbasugars by 6-exo-dig radical cyclisation reactions
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 cyclisat...
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Beilstein-Institut
2008-11-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.4.43 |
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doaj-36d7ea625e00471ead9ef9981dacc1402021-02-02T03:26:47ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972008-11-01414310.3762/bjoc.4.431860-5397-4-43Synthesis of chiral cyclohexanes and carbasugars by 6-exo-dig radical cyclisation reactionsRajeev K. Shrivastava0Elise Maudru1Gurdial Singh2Richard H. Wightman3Keith M. Morgan4Department of Chemistry, University of Sunderland, Sunderland, SR1 3SD, UKDepartment of Chemistry, University of Sunderland, Sunderland, SR1 3SD, UKDepartment of Chemistry, University of Sunderland, Sunderland, SR1 3SD, UKDepartment of Chemistry, Heriot-Watt University, Edinburgh, EH14 4AS, UK.Department of Chemistry, Heriot-Watt University, Edinburgh, EH14 4AS, UK.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.https://doi.org/10.3762/bjoc.4.43carbasugarscyclisationcyclohexanes6-membered ringstereoisomers |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Rajeev K. Shrivastava Elise Maudru Gurdial Singh Richard H. Wightman Keith M. Morgan |
| spellingShingle |
Rajeev K. Shrivastava Elise Maudru Gurdial Singh Richard H. Wightman Keith M. Morgan Synthesis of chiral cyclohexanes and carbasugars by 6-exo-dig radical cyclisation reactions Beilstein Journal of Organic Chemistry carbasugars cyclisation cyclohexanes 6-membered ring stereoisomers |
| author_facet |
Rajeev K. Shrivastava Elise Maudru Gurdial Singh Richard H. Wightman Keith M. Morgan |
| author_sort |
Rajeev K. Shrivastava |
| title |
Synthesis of chiral cyclohexanes and carbasugars by 6-exo-dig radical cyclisation reactions |
| title_short |
Synthesis of chiral cyclohexanes and carbasugars by 6-exo-dig radical cyclisation reactions |
| title_full |
Synthesis of chiral cyclohexanes and carbasugars by 6-exo-dig radical cyclisation reactions |
| title_fullStr |
Synthesis of chiral cyclohexanes and carbasugars by 6-exo-dig radical cyclisation reactions |
| title_full_unstemmed |
Synthesis of chiral cyclohexanes and carbasugars by 6-exo-dig radical cyclisation reactions |
| title_sort |
synthesis of chiral cyclohexanes and carbasugars by 6-exo-dig radical cyclisation reactions |
| publisher |
Beilstein-Institut |
| series |
Beilstein Journal of Organic Chemistry |
| issn |
1860-5397 |
| publishDate |
2008-11-01 |
| description |
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. |
| topic |
carbasugars cyclisation cyclohexanes 6-membered ring stereoisomers |
| url |
https://doi.org/10.3762/bjoc.4.43 |
| work_keys_str_mv |
AT rajeevkshrivastava synthesisofchiralcyclohexanesandcarbasugarsby6exodigradicalcyclisationreactions AT elisemaudru synthesisofchiralcyclohexanesandcarbasugarsby6exodigradicalcyclisationreactions AT gurdialsingh synthesisofchiralcyclohexanesandcarbasugarsby6exodigradicalcyclisationreactions AT richardhwightman synthesisofchiralcyclohexanesandcarbasugarsby6exodigradicalcyclisationreactions AT keithmmorgan synthesisofchiralcyclohexanesandcarbasugarsby6exodigradicalcyclisationreactions |
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1724307761631592448 |