A linchpin carbacyclization approach for the synthesis of carbanucleosides
- Author
- Leo M. H. Leung, Vicky Gibson and Bruno Linclau (UGent)
- Organization
- Abstract
- A convenient synthesis of carbanuclecosides, with both enantiomers equally accessible, is reported. The key step is a tandem linchpin cyclization process to give access to substituted carbafuranose derivatives having the correct relative stereochemistry for subsequent nucleobase introduction with inversion of configuration at C 1. This was illustrated by the synthesis of 2',3'-dideoxycarbathymidine via a convergent nucleobase introduction and of 2',3'-dideoxy-6'-hydroxycarbauridine via a linear nucleobase introduction. Both methods relied on Mitsunobu chemistry, and the first example of the Mukaiyama modification of the Mitsunobu reaction involving nucleobases as nucleophiles is reported.
- Keywords
- CARBOCYCLIC PYRIMIDINE NUCLEOSIDES, MITSUNOBU REACTION, OXIDATION-REDUCTION, ANTIVIRAL ACTIVITY, ASYMMETRIC-SYNTHESIS, SILYL, GROUP, ENANTIOSELECTIVE SYNTHESIS, STEREOSELECTIVE-SYNTHESIS, STEREOSPECIFIC SYNTHESIS, CHEMOENZYMATIC SYNTHESIS
Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-01GMMXAQYN10EP83N25DKRCAAS
- MLA
- Leung, Leo M. H., et al. “A Linchpin Carbacyclization Approach for the Synthesis of Carbanucleosides.” JOURNAL OF ORGANIC CHEMISTRY, vol. 73, no. 23, 2008, pp. 9197–206, doi:10.1021/jo801848h.
- APA
- Leung, L. M. H., Gibson, V., & Linclau, B. (2008). A linchpin carbacyclization approach for the synthesis of carbanucleosides. JOURNAL OF ORGANIC CHEMISTRY, 73(23), 9197–9206. https://doi.org/10.1021/jo801848h
- Chicago author-date
- Leung, Leo M. H., Vicky Gibson, and Bruno Linclau. 2008. “A Linchpin Carbacyclization Approach for the Synthesis of Carbanucleosides.” JOURNAL OF ORGANIC CHEMISTRY 73 (23): 9197–9206. https://doi.org/10.1021/jo801848h.
- Chicago author-date (all authors)
- Leung, Leo M. H., Vicky Gibson, and Bruno Linclau. 2008. “A Linchpin Carbacyclization Approach for the Synthesis of Carbanucleosides.” JOURNAL OF ORGANIC CHEMISTRY 73 (23): 9197–9206. doi:10.1021/jo801848h.
- Vancouver
- 1.Leung LMH, Gibson V, Linclau B. A linchpin carbacyclization approach for the synthesis of carbanucleosides. JOURNAL OF ORGANIC CHEMISTRY. 2008;73(23):9197–206.
- IEEE
- [1]L. M. H. Leung, V. Gibson, and B. Linclau, “A linchpin carbacyclization approach for the synthesis of carbanucleosides,” JOURNAL OF ORGANIC CHEMISTRY, vol. 73, no. 23, pp. 9197–9206, 2008.
@article{01GMMXAQYN10EP83N25DKRCAAS,
abstract = {{A convenient synthesis of carbanuclecosides, with both enantiomers equally accessible, is reported. The key step is a tandem linchpin cyclization process to give access to substituted carbafuranose derivatives having the correct relative stereochemistry for subsequent nucleobase introduction with inversion of configuration at C 1. This was illustrated by the synthesis of 2',3'-dideoxycarbathymidine via a convergent nucleobase introduction and of 2',3'-dideoxy-6'-hydroxycarbauridine via a linear nucleobase introduction. Both methods relied on Mitsunobu chemistry, and the first example of the Mukaiyama modification of the Mitsunobu reaction involving nucleobases as nucleophiles is reported.}},
author = {{Leung, Leo M. H. and Gibson, Vicky and Linclau, Bruno}},
issn = {{0022-3263}},
journal = {{JOURNAL OF ORGANIC CHEMISTRY}},
keywords = {{CARBOCYCLIC PYRIMIDINE NUCLEOSIDES,MITSUNOBU REACTION,OXIDATION-REDUCTION,ANTIVIRAL ACTIVITY,ASYMMETRIC-SYNTHESIS,SILYL,GROUP,ENANTIOSELECTIVE SYNTHESIS,STEREOSELECTIVE-SYNTHESIS,STEREOSPECIFIC SYNTHESIS,CHEMOENZYMATIC SYNTHESIS}},
language = {{eng}},
number = {{23}},
pages = {{9197--9206}},
title = {{A linchpin carbacyclization approach for the synthesis of carbanucleosides}},
url = {{http://doi.org/10.1021/jo801848h}},
volume = {{73}},
year = {{2008}},
}
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