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Isolierung, Konstitution und Synthese der (R)‐(−)‐Eucominsäure

 

作者: Werner Heller,   Christoph Tamm,  

 

期刊: Helvetica Chimica Acta  (WILEY Available online 1974)
卷期: Volume 57, issue 6  

页码: 1766-1784

 

ISSN:0018-019X

 

年代: 1974

 

DOI:10.1002/hlca.19740570628

 

出版商: WILEY‐VCH Verlag GmbH

 

数据来源: WILEY

 

摘要:

AbstractFrom the bulbs ofEucomis punctata L'Hérit. (Liliaceae) and of a hitherto undefined species ofEucomisa new optically active phenolic carboxylic acid, eucomic acid, was isolated. Structure1was assigned on the basis of chemical and spectral evidence. The absolute configuration of eucomic acid was determined by its correlation with piscidic acid ((2R, 3S)‐2‐(4′‐hydroxybenzyl)‐tartaric acid) (8). Consequently, eucomic acid is (R)‐(−)‐2‐(4′‐hydroxybenzyl)‐malic acid (1). For the stereospecific synthesis, methylcis‐p‐methoxybenzylidene‐succinic acid (22) was transformed into the γ‐lactone24which, by catalytic hydrogenolysis, yielded (±)‐2‐(4′‐hydroxybenzyl)‐malic acid 1‐methyl ester (27). Resolution with (−)‐quinine led to the enantiomeric acids29and30. The methyl ester of the levorotatory enantiomer30was identical w

 

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