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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 21
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Original Articles

Efficient Synthesis of New Nucleoside Analogues with a Methylenecyclobutane Unit

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Pages 3225-3239 | Received 29 Mar 2006, Published online: 24 Nov 2006
 

Abstract

Synthesis of eight nucleoside analogues 411 with a methylenecyclobutane unit is described. Wittig reaction with 2‐hydroxymethylcyclobutanone 12 gave a mixture of Z (13) and E (14) derivatives, which was separated before functional modifications. The heterocyclic moieties were introduced via a Mitsunobu reaction either on the saturated chain or on the unsaturated chain. When adenine was used in this reaction, only the N‐9 substitution products were obtained. Removal of the protecting groups provided the target products.

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