A common and versatile synthetic route to (−) and (+) pentenomycin I, (+) halopentenomycin I and dehydropentenomycin

•Total synthesis of (−) and (+) pentenomycin I, (+) halopentenomycin I and dehydropentenomycin.•Stereoselective hydroxymethylation, stereoselective Grignard reaction and RCM reaction.•Functionalized polyhydroxylated five-membered carbocycles.

A versatile and stereoselective total synthesis of (+) and (−) pentenomycin I, (+) halopentenomycins I and dehydropentenomycin from a common chiral polyhydroxylated cyclopentene through oxidation and protection/deprotection has been described. Stereoselective hydroxymethylation, stereoselective Grignard reaction and ring closing metathesis are the key features of our approach.

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