YAKHAK HOEJI (약학회지)

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

An Approach to the Enantioselective Synthesis of the Crucial Intermediate of Conformationally Locked Nucleosides

형태학적으로 고정된 뉴클레오사이드 주요중간체의 Enantioselective 합성법 탐색

  • Kim, Soon-Ai (College of Pharmacy, Institute of Pharmaceutical Research and Development, Wonkwang University) ;
  • Kim, Hak-Sung (College of Pharmacy, Institute of Pharmaceutical Research and Development, Wonkwang University)
  • Received : 2010.11.01
  • Accepted : 2010.11.08
  • Published : 2010.12.31
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Abstract

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.

Keywords

References

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