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(–)‐Methyl Cucurbate and (–)‐Methyl Jasmonate by Kinetic Resolution
Author(s) -
Borm Claudia,
Winterfeldt Ekkehard
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960722
Subject(s) - chemistry , enantiopure drug , kinetic resolution , methyl jasmonate , cyclopentenone , adduct , catalysis , dimethyl malonate , organic chemistry , pyridinium chlorochromate , methacrolein , malonate , alkylation , sodium borohydride , medicinal chemistry , palladium , enantioselective synthesis , methacrylic acid , biochemistry , polymer , monomer , gene
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 ).