Synthesis of a Carbohydrate-Derived 1-Oxaspiro[4.4]Nonane Skeleton and Its Conversion into Spironucleosides
IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata
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| Title |
Synthesis of a Carbohydrate-Derived 1-Oxaspiro[4.4]Nonane Skeleton and Its
Conversion into Spironucleosides
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| Creator |
Maity, Joy Krishna
Achari, Basudeb Drew, Michael G B Mandal, Sukhendu B |
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| Subject |
Chemistry
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| Description |
An easy entry to the 1-oxaspiro[4.4]nonane skeleton has
been developed starting from a D-glucose-derived substrate. The
key steps involve (a) installation of olefin moieties at the appropriate
places through simple transformations and (b) construction of
spiro rings by utilizing ring-closing metathesis reactions between
these olefin functionalities. Subsequent deprotection of the
acetonide functionality, peracetylation, nucleosidaton under
Vorbrüggen reaction conditions, and final deprotections result in
the formation of the spironucleosides. The involvement of an interesting
intra/intermolecular acetyl migration has been used to rationalize
the product distribution during desilylation. Various 1D and
2D NMR techniques and X-ray analyses of some important intermediates
were used for assigning the structures and stereochemistry
of the products.
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| Date |
2010
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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/19/1/SYNTHESIS%2DSTUTTGART_(15)_2533%2D2542;2010[53].pdf
Maity, Joy Krishna and Achari, Basudeb and Drew, Michael G B and Mandal, Sukhendu B (2010) Synthesis of a Carbohydrate-Derived 1-Oxaspiro[4.4]Nonane Skeleton and Its Conversion into Spironucleosides. Synthesis, 15. pp. 2533-2542. |
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| Relation |
http://dx.doi.org/10.1055/s-0029-1218828
http://www.eprints.iicb.res.in/19/ |
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