Sequential Ring-Closing Metathesis and Nitrone Cycloaddition on Glucose-Derived Substrates: A Divergent Approach to Analogues of Spiroannulated Carbanucleosides and Conformationally Locked Nucleosides
IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata
View Archive Info| Field | Value | |
| Title |
Sequential Ring-Closing Metathesis and Nitrone Cycloaddition on Glucose-Derived Substrates: A Divergent Approach to Analogues of Spiroannulated Carbanucleosides and Conformationally Locked Nucleosides
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| Creator |
Sahabuddin, Sk
Roy, Ashim Drew, Michael G. B Roy, Biswajit Gopal Achari, Basudeb Madal, Sukhendu B |
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| Subject |
Chemistry
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| Description |
The carbohydrate-derived substrate 3-C-allyl-1,2:5,6-di-O-isopropylidene-R-D-allofuranose was judiciously
manipulated for preparing suitable synthons, which could be converted to a variety of isoxazolidinospirocycles
and -tricycles through the application of ring-closing metathesis (RCM) and intramolecular nitrone cycloaddition (INC) reactions. Cleavage of the isoxazolidine rings of some of these derivatives by tranfer hydrogenolysis followed by coupling of the generated amino functionalities with 5-amino- 4,6-dichloropyrimidine furnished the corresponding chloropyrimidine nucleosides, which were elaborated to spiroannulated carbanucleosides and conformationally locked bicyclo[2.2.1]heptane/oxa-bicyclo[3.2.1]- octane nucleosides. However, use of higher temperature for the cyclization of one of the chloropyrimidines led to the dimethylaminopurine analogue as a sole product, formed via nucleophilic displacement of the chloro group by dimethylamine generated from DMF.
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| Publisher |
American Chemical Society
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| Date |
2006
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| Type |
Article
PeerReviewed |
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| Format |
application/pdf
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| Identifier |
http://www.eprints.iicb.res.in/405/1/JOURNAL_OF_ORGANIC_CHEMISTRY%2C__71(_16)%2C_5980%2D5992_[51].pdf
Sahabuddin, Sk and Roy, Ashim and Drew, Michael G. B and Roy, Biswajit Gopal and Achari, Basudeb and Madal, Sukhendu B (2006) Sequential Ring-Closing Metathesis and Nitrone Cycloaddition on Glucose-Derived Substrates: A Divergent Approach to Analogues of Spiroannulated Carbanucleosides and Conformationally Locked Nucleosides. The Journal of Organic Chemistry, 71 (16). pp. 5980-5992. |
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| Relation |
http://dx.doi.org/10.1021/jo0606554 CCC: $33.50
http://www.eprints.iicb.res.in/405/ |
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