An enantiospecific synthesis of (+)-methyl epijasmonate and (-)-methyl cucurbate from L-glutamic acid

Article abstract of DOI:10.1016/S0040-4020(98)00069-6

An enantiospecific route to jasmonoid natural products, (+) - methyl epijasmonate and (-) -methyl cucurbate from L-glutamic acid is reported. The key step is a 5-(3,4) ene cyclization of a functionalized 1,6-diene as chiron, which sets up three chiral centres with a high degree of diastereoselectivity.