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The first, general and efficient route has been developed for the synthesis of N-((E,3S,4R)-5benzylidene-tetrahydro-4-hydroxy-6-oxo-2H-pyran-3-yl) palmitamide, a lactone ceramide analogue from (S)-Garner aldehyde-methyl acrylate derived Baylis-Hillman adduct with anti configuration. Reaction conditions have been optimized for the Heck reaction of iodobenzene on Baylis-Hillman adduct with anti configuration to obtain the protected aromatic ceramide analogue intermediate which subsequently on deprotection and N-acylation provided the lactone ceramide analogue. Further, various substituted phenyl iodides have also been employed in the Heck reaction under the optimized conditions for the synthesis of few protected aromatic ceramide analogues intermediates to the test efficacy of the developed methodology.

(S)-Garner aldehyde derived Baylis-Hillman adduct: a substrate for the synthesis of a lactone ceramide analogue via a sequential Heck reaction