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Lewis acid mediated Diels-Alder reactions of 6-vinylpurines

✍ Scribed by Anniken T. Øver»s; Lise-Lotte Gundersen; Frode Rise

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 692 KB
Volume: 53
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(96)01089-7

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✦ Synopsis

6-Vinylpurines readily undergo Diels-Alder reactions with dienes. Both reactivity and endo selectivity are greatly improved when the cycloadditions are performed in the presence of zinc chloride. Lewis acid mediated Diels-Alder reaction of 6-vinylpurine riboside was employed as a key step in the synthesis of a nucleoside with structural resemblance to potent A, adenosine agonists.

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