Synthesis of purine-and pyrimidine-substituted heptadienes. The stereochemistry of cyclization and cyclopolymerization products

JY Tsai, KH Bouhadir, JL Zhou, TR Webb…

Index: Tsai, Jui-Yi; Bouhadir, Kamal Hani; Zhou, Jing-Lan; Webb, Thomas R.; Sun, Yahong; Shevlin, Philip B. Journal of Organic Chemistry, 2003 , vol. 68, # 4 p. 1235 - 1241

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Citation Number: 14

Abstract

A series of 1, 6-heptadienes, substituted in the 4 position with nucleic acid bases 1-6, have been synthesized via Mitsunobu condensations. Guanine, adenine, thymine, and uracil derivatives can be prepared directly by coupling the protected base with 1, 6-heptadien-4-ol (7). However, coupling protected cytosine and 7 gives an O-alkylated product. Thus, the cytosine derivative must be prepared from the uracil-substituted heptadienes via the ...

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