Synthesis of (+/-)-2,3-Methanoproline: A Novel Inhibitor of Ethylene Biosynthesis

Article abstract of DOI:10.1016/S0040-4020(01)85122-X

The title compound, 2-aza-bicyclo<3.1.0>hexane-1-carboxylic acid (2) was prepared by treatment of N-benzyloxycarbonyl-2,3-dehydroproline tert-butyl ester with diazomethane followed by photolysis of the resulting pyrazoline and deprotection.Its N-acetyl-N'-methyl amide, a peptide mimic, was synthesized and the structure of was confirmed by X-ray diffraction studies.NMR spectroscopy was also used to examine the effect of the cyclopropane ring on its conformation.This 2,3-methanoamino acid (2) was found to be a weak inhibitor of ethylene biosynthesis in cucumber cotyledon strips and germinating squash seeds.The data show that 2 probably inhibits the conversion of 1-aminocyclopropanecarboxylic acid to ethylene in these tissues.