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
(2012)Doi:10.1139/v65-024
(1965)Doi:10.1016/S0040-4039(98)01901-7
(1998)Doi:10.1016/S0040-4039(98)02000-0
(1998)Doi:10.1055/s-0036-1591566
(2018)Doi:10.1021/om980823l
(1998)
