Synthesis 1988; 1988(4): 310-313
DOI: 10.1055/s-1988-27551
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
20 August 2002 (online)

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.