1-Fluorocycloalkanecarboxylic Acids in the Synthesis of 16-Achiral 16-Fluoro-9a-carbaprostacyclin Derivatives

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Abstract
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.

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