180308-62-7Relevant academic research and scientific papers
(-)-Methyl cucurbate and (-)-methyl jasmonate by kinetic resolution
Borm, Claudia,Winterfeldt, Ekkehard
, p. 1209 - 1212 (2007/10/03)
The kinetic resolution of a malonate-substituted cyclopentenone gave rise to the formation of an enantiopure Diels-Alder adduct which was converted into methyl dehydrocucurbate 2 by diastereoselective alkylation with (Z)-1-bromo-2-pentene and subsequent borohydride reduction. Selective hydrogenation of 2 with a palladium/calcium carbonate catalyst proved to be a reliable route to (-)-methyl cucurbate (1) the oxidation of which with pyridinium chlorochromate and subsequent treatment with acid afforded (-)-methyl jasmonate (9). VCH Verlagsgesellschaft mbH, 1996.
