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Synthesis 1994; 1994(8): 792-794
DOI: 10.1055/s-1994-25576
short paper
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Synthesis of Prostaglandins III:1 Efficient and Practical Synthesis of Antisecretory Prostaglandin Enprostil

Yong Sup Lee* , Kee Hong Nam, Sun Ho Jung, Hokoon Park
  • *Organic Chemistry Laboratory (I), Korea Institute of Science & Technology, P.O. Box 131 Cheongryang, Seoul 130-650, Korea
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Publication Date:
17 September 2002 (online)

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An efficient and practical 8-step synthesis of enprostil (1) starting from the lactone 2 has been developed. The propargylic acetate 5 was prepared from the lactol 3 by the reaction with ethynylmagnesium bromide followed by acetylation. Propargylic acetate 5 was converted into enprostil (1) via the introduction of an allene moity by reaction with a Grignard reagent in the presence of a CuI · P(OEt)3 complex.