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Synlett 1999; 1999(11): 1757-1759
DOI: 10.1055/s-1999-2953
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Efficient Route to Functionalized Eight-Membered Lactones Based on Intramolecular Silicon-Directed Acylative Ring-Opening Reactions of 3-(Tetrahydro-2-furyl)propanoic Acid Derivatives

Hidenori Ohi* , Susumu Inoue, Yoshiharu Iwabuchi, Hiroshi Irie, Susumi Hatakeyama
  • *Faculty of Pharmaceutical Sciences, Nagasaki University, Nagasaki 852-8521, Japan; Fax 81-95-8 48-42 86; E-mail: susumi@net.nagasaki-u.ac.jp
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Publication Date:
31 December 1999 (online)

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Exposure of 3-(tetrahydro-2-furyl)-3-trimethylsilylpropanoic acids and 3-(2-trimethylsilylmethyltetrahydro-2-furyl)propanoic acids to trifluoroacetic anhydride allows intramolecular acylative ring-opening reaction to give the corresponding eight-membered lactones in moderate to good yields.

eight-membered lactones - silicon compounds - ring enlargement - acyloxonium ion - octalactin analogs