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A new methodology for the synthesis of carbofuranoses and related carbanucleosides

A new methodology for the synthesis of carbofuranoses and related carbanucleosides
A new methodology for the synthesis of carbofuranoses and related carbanucleosides

Carbocyclic nucleosides (carbanucleosides) are mimetics of natural nucleosides and have been the subject of intense research in recent years.  Many analogues of carbanucleosides have exhibited potent anti-viral and anti-tumour properties.  Thus, there is a continuing interest for synthetic methodologies to access carbanucleosides analogues in enantiomerically pure form.  (Fig. 14249)

This thesis describes the development of a novel approach for the enantiospecific synthesis of carbafuranose analogues and the conversion of the synthesised carbafuranoses into the corresponding carbanucleosides.  The core of the methodology concerns the construction of the cyclopentane moiety of the carbanucleoside by a Brook rearrangement-mediated domino carbacyclisation.  Hence, the coupling of a lithio-tert-butyldimethyl-1,3-dithiane linchpin with chiral symmetric bis-epoxide substrates led to highly functionalised spiro-thioketals which could be converted to a range of carbafuranose analogues in straightforward transformations.  The symmetric bis-epoxide building blocks were synthesised from arabitol, which is available in both enantiomeric forms.  The hetereonucleobase of the carbanucleoside was then introduced to the suitably protected cycloalkanols to afford the corresponding carbanucleoside targets.

University of Southampton
Leung, Leo Man Ho
fee69f6b-3102-43d2-97ad-0c802bccfc26
Leung, Leo Man Ho
fee69f6b-3102-43d2-97ad-0c802bccfc26

Leung, Leo Man Ho (2006) A new methodology for the synthesis of carbofuranoses and related carbanucleosides. University of Southampton, Doctoral Thesis.

Record type: Thesis (Doctoral)

Abstract

Carbocyclic nucleosides (carbanucleosides) are mimetics of natural nucleosides and have been the subject of intense research in recent years.  Many analogues of carbanucleosides have exhibited potent anti-viral and anti-tumour properties.  Thus, there is a continuing interest for synthetic methodologies to access carbanucleosides analogues in enantiomerically pure form.  (Fig. 14249)

This thesis describes the development of a novel approach for the enantiospecific synthesis of carbafuranose analogues and the conversion of the synthesised carbafuranoses into the corresponding carbanucleosides.  The core of the methodology concerns the construction of the cyclopentane moiety of the carbanucleoside by a Brook rearrangement-mediated domino carbacyclisation.  Hence, the coupling of a lithio-tert-butyldimethyl-1,3-dithiane linchpin with chiral symmetric bis-epoxide substrates led to highly functionalised spiro-thioketals which could be converted to a range of carbafuranose analogues in straightforward transformations.  The symmetric bis-epoxide building blocks were synthesised from arabitol, which is available in both enantiomeric forms.  The hetereonucleobase of the carbanucleoside was then introduced to the suitably protected cycloalkanols to afford the corresponding carbanucleoside targets.

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Published date: 2006

Identifiers

Local EPrints ID: 466191
URI: http://eprints.soton.ac.uk/id/eprint/466191
PURE UUID: b0c9b8de-eb05-4d2b-acfc-d857ee76f89f

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Date deposited: 05 Jul 2022 04:42
Last modified: 16 Mar 2024 20:33

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Author: Leo Man Ho Leung

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