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Ein alternativer Zugang zum PQQ‐Triester
Author(s) -
Sicker Dieter,
Stehfest Ekkehard,
Wilde Horst,
Martin Pierre
Publication year - 1996
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19960790309
Subject(s) - chemistry , annulation , quinoline , block (permutation group theory) , redox , stereochemistry , catalysis , organic chemistry , geometry , mathematics
An Alternative Approach to the PQQ‐Triester A novel approach to triethyl 5‐methoxy‐1 H ‐pyrrolo[2,3‐ f ]quinoline‐2,7,9‐tricarboxylate ( 6 ), a close precursor of the redox cofactor PQQ of bacterial dehydrogenases, is described. Diethyl 2‐oxopent‐3‐ynedioate ( 5 ) was used as building block for the annelation of the quinoline unit. The annelation proceeds in two steps via the diastereoselective formation of diethyl ( Z )‐4‐{[2‐(ethoxycarbonyl)‐5‐methoxyindol‐6‐yl]amiono}‐2‐oxopent‐3‐enedioate (( Z )‐ 7 ) followed by acid‐catalyzed cyclocondensation.