A convergent approach for the synthesis of fluorinated sphingosine analogues

An improved route to a fluorinated analogue of sphingosine has been developed starting from Garner’s aldehyde with two cross-metathesis couplings and an electrophilic fluorodesilylation as the key steps. This approach eliminates the problem of double bond transposition encountered with strategies relying on the nucleophilic fluorinating reagent DAST and supplies the target compound as well as a fluorinated intermediate amenable to functional variations at three sites.

Abstract licence: CC BY

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