EventsThe 12th International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-12-01238
This submission belongs to the session c. Bioorganic Chemistry and Natural Products of the event The 12th International Electronic Conference on Synthetic Organic Chemistry
Published date
29 Nov, 2008
Citation
Paula Abeijón, José M. Blanco, Olga Caamaño, Franco Fernández, Marcos D. García, Xerardo García-Mera, A convenient synthesis of new 6-substituted purinylcarbanucleosides on cyclopenta[b]thiophene, in Proceedings of The 12th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2008, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-12-01238
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A convenient synthesis of new 6-substituted purinylcarbanucleosides on cyclopenta[b]thiophene

Paula Abeijón 1
José M. Blanco 1
Olga Caamaño 1
Franco Fernández 1
Marcos D. García 2
Xerardo García-Mera 1
1. Departamento de Química Orgánica, Facultade de Farmacia, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain
2. Departmento de Química Fundamental, Facultade de Ciencias, Campus da Zapateira s/n, 15701 A Coruña, Spain
Abstract
The first members of a new family of heterocarbobicyclic nucleoside analogues have been synthesized from the cis/trans mixture of (4-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-6-yl)methanols cis/trans-7. The separation of cis and trans intermediates during preparation of the 6-chloropurine derivatives allowed separate preparation of the purine heterocarbanucleosides cis-10 and trans-11, from which cis-(12-14) and trans-(16-18) were obtained by replacement of the 6-chloro substituent with amino, hydroxy and cyclopropylamino groups. Additionally, the 6-phenyl-purinyl analogues cis-15 and trans-19 were prepared from cis-10 and trans-11 using Suzuki-Miyaura methodology.
Keywords
n/a
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