Bulletin of the Korean Chemical Society

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An Efficient Synthesis of 12-epi-Carbacyclins Using a Palladium-Mediated Tandem Alkene Insertion Strategy

  • Lee, Nam-Ho (Department of Chemistry, Cheju National University) ;
  • Larock, Richard C. (Department of Chemistry, Iowa State University)
  • Published : 2002.01.20
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Abstract

A short synthesis of novel prostanoids, 12-epi-carbacyclins 3 and 24, has been accomplished using palladium chemistry as a key step. The silyl enol ether 10a prepared through organopalladium chemistry has been allowed to react with 1-octen-3-one in the presence of $Pd(OAc)_2$ to give compound 12 in a single step. The unusual chemo- and stereoselective reduction of the ${\alpha},{\beta}$-unsaturated ketone in 12 has been effected with (S)-BINALH. Subsequent desilylation and Wittig reaction have provided the Subsequent desilylation and Wittig reaction have provided the $PGI_2$ analogues 3 and 24.

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References

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