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KMID : 0370220100540060474
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Yakhak Hoeji
2010 Volume.54 No. 6 p.474 ~ p.480
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An Approach to the Enantioselective Synthesis of the Crucial Intermediate of Conformationally Locked Nucleosides
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Kim Soon-Ai
Kim Hak-Sung
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Abstract
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Conformationally locked nucleosides are important in searching selective agonists and antagonists for P2Y receptors. There were two previous synthetic works of the crucial intermediate, cyclopentenyl alcohol (3), which had some inefficiency like using too strong dianionic base and synthesis of racemate. Here we describes a facile synthesis of the intermediate using Sharpless epoxidation and the opening of epoxide ring using zinc, followed by Grubb’s metathesis as key steps. The intermediate was converted to the southern bicyclo[3.2.0]heptane for confirming its usefulness.
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KEYWORD
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nucleoside, enantioselective, Sharpless oxidation, bicyclo[3.2.0]heptane
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