Tetrahedron Letters p. 8373 - 8376 (1998)
Update date:2022-08-04
Topics:
Zhou, Jinglan
Shevlin, Philip B.
A convenient synthesis of racemic 2'-deoxy carbocyclic thymidines lacking the 5'-methylene group is reported. Thus, appropriately protected nucleic acid bases are coupled to 3-cyclopentenol, 1, via the Mitsunobu reaction. Epoxidation of the protected thymine substituted cyclopentene gives the corresponding syn and anti-epoxides in a 4:1 ratio. Ring opening of the syn-epoxide by a variety of nucleophiles leads to the racemic 2'-deoxy carbocyclic thymidines lacking the 5'-methylene group.
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Doi:10.1021/ja301334b
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(1998)
