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Enantioselective Synthesis and Cytotoxic Evaluation of 4,5‐Dihydro‐5‐[aryl(hydroxy)methyl]‐3‐methylidenefuran‐2(3 H )‐ones
Author(s) -
Janecki Tomasz,
Albrecht Anna,
Warzycha Edyta,
Studzian Kazimierz,
Janecka Anna,
Krajewska Urszula,
Różalski Marek
Publication year - 2005
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200590096
Subject(s) - chemistry , aryl , enantiomer , stereochemistry , enantioselective synthesis , sharpless asymmetric dihydroxylation , cytotoxic t cell , dihydroxylation , in vitro , organic chemistry , biochemistry , catalysis , alkyl
A series of enantiomerically enriched 4,5‐dihydro‐5‐[aryl(hydroxy)methyl]‐3‐methylidenefuran‐2(3 H )‐ones ( 8 ) were synthesized by means of asymmetric Sharpless dihydroxylation of the 2‐phosphorylated 5‐aryl‐pent‐4‐enoic acids 13 , followed by Horner – Wadsworth – Emmons reaction of the resulting furanones 15 ( Scheme 2 ). An enantiomeric excess (ee) of 20–95% was achieved for compounds 8 , and their absolute configurations were determined by the Mosher ester method. Cytotoxic evaluation against L‐1210 and HL‐60 leukemia cell lines revealed that the target compounds 8 are active in the micromolar concentration range ( Table 2 ). Thereby, significant differences in activity between the corresponding enantiomers were observed for the HL‐60 cell line.