The first total syntheses of four stereoisomers of 13-hydroxy-14-methylhexadecanoic acid have been accomplished. Central to this strategy are asymmetric alkynylation of aldehyde, acid-catalyzed lactonization, the selective protection of primary alcohol and Wittig reaction. The product 1a was obtained in 17 steps in 2% overall yield. Moreover, these synthetic chiral hydroxy fatty acids 1a-1d are valuable for the development of antibacterial agents.

This study successfully synthesized four stereoisomers of 13-hydroxy-14-methylhexadecanoic acid, providing valuable compounds for developing antibacterial agents.

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Asymmetric syntheses of four stereoisomers of 13-hydroxy-14-methylhexadecanoic acid as potential antibacterial agents.

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