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Synthesis 1988; 1988(4): 310-313
DOI: 10.1055/s-1988-27551
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1-Fluorocycloalkanecarboxylic Acids in the Synthesis of 16-Achiral 16-Fluoro-9a-carbaprostacyclin Derivatives

Nicola Mongelli* , Fabio Animati, Roberto D'Alessio, Leandro Zuliani, Carmelo Gandolfi
  • *FARMITALIA CARLO ERBA S.p.A., Ricerca e Sviluppo Chimico, Via C. Imbonati 24, I-20159 Milano, Italy
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Publication Date:
20 August 2002 (online)

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Introduction of a fluorine atom into position 16 of the ω-chain is a useful tool for modulation of biological activity in the prostanoid field. We devised a facile, four-step synthesis of 1-fluorocyclohexanecarboxylic acid, a precursor of phosphoranes and phosphonates required for building up the ω-chain of the fluorinated prostacyclin 1. This method is generally applicable to the synthesis of α-fluoro-α-branched carboxylic acids from ketones.