Studies on chrysanthemic acid. XXVII Synthesis of optically active dihydorchrysanthenolactone by asymmetric decomposition of unsaturated diazoacetic ester.

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Abstract
Dihydrochrysanthemolactone was synthesized by copper catalyzed decomposition of 2, 5-dimethyl-4-hexen-2-yl diazoacetate, which had been prepared by the reaction between tosylhydrazone of glyoxyl chloride and 2, 5-dimethyl-4-hexen-2-ol. The tertiary alcohol was derived in five steps from isoprene via the Grignard reaction of methyl 4-methyl-3-pentenoate. The decomposition of the diazoacetate using a chiral salicylaldiminatocopper (II) complex containing an (R)-D-phenylalaniol derivative as an amine ligand gave the optically active dihydrochrysanthemolactone in 34% optical yield.

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