Stereoselective synthesis of carbocyclic analogues of the nucleoside Q precursor (PreQ0)

A convergent and stereoselective synthesis of chiral cyclopentyl- and cyclohexylamine derivatives of nucleoside Q precursor (PreQ0) has been accomplished. This synthetic route allows for an efficient preparation of 4-substituted analogues with interesting three-dimensional character, including chira...

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Main Authors: Sabin Llona-Minguez, Simon P. Mackay
Format: Article
Language:English
Published: Beilstein-Institut 2014-06-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
Online Access:https://doi.org/10.3762/bjoc.10.135
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author Sabin Llona-Minguez
Simon P. Mackay
author_facet Sabin Llona-Minguez
Simon P. Mackay
author_sort Sabin Llona-Minguez
collection DOAJ
description A convergent and stereoselective synthesis of chiral cyclopentyl- and cyclohexylamine derivatives of nucleoside Q precursor (PreQ0) has been accomplished. This synthetic route allows for an efficient preparation of 4-substituted analogues with interesting three-dimensional character, including chiral cyclopentane-1,2-diol and -1,2,3-triol derivatives. This unusual substitution pattern provides a useful starting point for the discovery of novel bioactive molecules.
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spelling doaj.art-f6a5198eb26f4f25862d9823e031a2fd2022-12-21T23:27:54ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-06-011011333133810.3762/bjoc.10.1351860-5397-10-135Stereoselective synthesis of carbocyclic analogues of the nucleoside Q precursor (PreQ0)Sabin Llona-Minguez0Simon P. Mackay1Strathclyde Institute of Pharmacy & Biomedical Sciences, University of Strathclyde, 165 Cathedral Street, Glasgow, G4 0RE, United KingdomStrathclyde Institute of Pharmacy & Biomedical Sciences, University of Strathclyde, 165 Cathedral Street, Glasgow, G4 0RE, United KingdomA convergent and stereoselective synthesis of chiral cyclopentyl- and cyclohexylamine derivatives of nucleoside Q precursor (PreQ0) has been accomplished. This synthetic route allows for an efficient preparation of 4-substituted analogues with interesting three-dimensional character, including chiral cyclopentane-1,2-diol and -1,2,3-triol derivatives. This unusual substitution pattern provides a useful starting point for the discovery of novel bioactive molecules.https://doi.org/10.3762/bjoc.10.135diol synthesisnucleosidePreQ0stereoselective amine synthesistriol synthesis
spellingShingle Sabin Llona-Minguez
Simon P. Mackay
Stereoselective synthesis of carbocyclic analogues of the nucleoside Q precursor (PreQ0)
Beilstein Journal of Organic Chemistry
diol synthesis
nucleoside
PreQ0
stereoselective amine synthesis
triol synthesis
title Stereoselective synthesis of carbocyclic analogues of the nucleoside Q precursor (PreQ0)
title_full Stereoselective synthesis of carbocyclic analogues of the nucleoside Q precursor (PreQ0)
title_fullStr Stereoselective synthesis of carbocyclic analogues of the nucleoside Q precursor (PreQ0)
title_full_unstemmed Stereoselective synthesis of carbocyclic analogues of the nucleoside Q precursor (PreQ0)
title_short Stereoselective synthesis of carbocyclic analogues of the nucleoside Q precursor (PreQ0)
title_sort stereoselective synthesis of carbocyclic analogues of the nucleoside q precursor preq0
topic diol synthesis
nucleoside
PreQ0
stereoselective amine synthesis
triol synthesis
url https://doi.org/10.3762/bjoc.10.135
work_keys_str_mv AT sabinllonaminguez stereoselectivesynthesisofcarbocyclicanaloguesofthenucleosideqprecursorpreq0
AT simonpmackay stereoselectivesynthesisofcarbocyclicanaloguesofthenucleosideqprecursorpreq0