Abstract
AbstractFrom the bulbs of Eucomis punctata L'Hérit. (Liliaceae) and of a hitherto undefined species of Eucomis a new optically active phenolic carboxylic acid, eucomic acid, was isolated. Structure 1 was assigned on the basis of chemical and spectral evidence. The absolute configuration of eucomic acid was determined by its correlation with piscidic acid ((2 R, 3 S)‐2‐(4′‐hydroxybenzyl)‐tartaric acid) (8). Consequently, eucomic acid is (R)‐(−)‐2‐(4′‐hydroxybenzyl)‐malic acid (1). For the stereospecific synthesis, methyl cis‐p‐methoxybenzylidene‐succinic acid (22) was transformed into the γ‐lactone 24 which, by catalytic hydrogenolysis, yielded (±)‐2‐(4′‐hydroxybenzyl)‐malic acid 1‐methyl ester (27). Resolution with (−)‐quinine led to the enantiomeric acids 29 and 30. The methyl ester of the levorotatory enantiomer 30 was identical with the dimethyl ester 3 of 4′‐O‐methyl‐eucomic acid.
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