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A Straightforward Stereoselective Synthesis of d- and l-5-Hydroxy-4-hydroxymethyl-2-cyclohexenylguanine

Wang, Jing, Morral-Cardoner, Jordi, Hendrix, Chris and Herdewijn, Piet (2001) A Straightforward Stereoselective Synthesis of d- and l-5-Hydroxy-4-hydroxymethyl-2-cyclohexenylguanine. The Journal of Organic Chemistry, 66 (25). pp. 8478-8482. ISSN 00223263

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Abstract

A novel and facile synthesis of 5-hydroxy-4-hydroxymethyl-2-cyclohexenylguanine 1 is described. The key steps involve a Diels−Alder reaction of ethyl (2E)-3-acetyloxy-2-propenoate 2 as dienophile with Danishefsky's diene 3 to build up the six-membered ring skeleton, a Fraser-Reid reductive rearrangement of the adduct using LiAlH4, and base-moiety introduction using a Mitsunobu reaction. Optically pure d- and l-1 were obtained via resolution of intermediate 7 with (R)-(−)-methylmandelic acid. The synthetic procedure toward racemic 1 consists of only five steps and has proven to be highly efficient toward the synthesis of cyclohexenyl nucleosides.

Item Type: Article
Additional Information: Reprinted with permission from {Journal of Organic Chemistry}. Copyright {2001} American Chemical Society.
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Schools: School of Applied Sciences
Related URLs:
Depositing User: Sara Taylor
Date Deposited: 30 Jun 2011 09:00
Last Modified: 30 Jun 2011 09:00
URI: http://eprints.hud.ac.uk/id/eprint/10836

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