The first enantioselective total synthesis of seimatopolide B has been achieved, using ring-closing metathesis and DCC (N,N9-dicyclohexylcarbodiimide) coupling as key steps. The stereogenic centres were generated by means of iterative hydrolytic kinetic resolution (HKR) of racemic epoxides.

An efficient synthesis of (5R,6S)-tert-butyl 5-acetoxy-6-(hydroxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate 1, a common intermediate for various polyhydroxylated piperidines is reported in six steps with 32% overall yield starting from Garner's aldehyde. The key steps include the diastereoselective nucleophilic addition and intramolecular cyclization. (5R,6S)-tertbutyl 5-acetoxy-6-(hydroxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate is a common precursor for the synthesis of 1-deoxy-L-mannojirimycin, 1-deoxy-L-idonojirimycin, Lfagomycin and related analogues.