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Synlett 1998; 1998(8): 930-932
DOI: 10.1055/s-1998-1819
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Synthesis of Optically Active Cyclopenta[b]benzofuran as a Precursor of m-Phenyleneprostacyclin

Hisao Nishiyama* , Naoya Sakata, Hayato Sugimoto, Yukihiro Motoyama, Hisanori Wakita, Hiroshi Nagase
  • *School of Materials Science, Toyohashi University of Technology, Tempaku-cho, Toyohashi 441-8580, Japan; Fax 0532-48-5833
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Publication Date:
31 December 2000 (online)

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The optically pure cyclopenta[b]benzofuran derivatives (-)-1 and (-)-2 were synthesized from (+)-(1S,4R)-cis-4-acetoxy-2-cyclopenten-1-ol [(+)-3] via sequential Mitsunobu reaction and palladium-catalyzed allylic substitution with phenol derivatives followed by SN2′ intramolecular cyclization.

cyclopentabenzofuran - prostacyclin - Mitsunobu reaction - palladium-catalyzed allylic etherification - enantioselective reaction