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Ein alternativer Zugang zum PQQ-Triester

✍ Scribed by Dieter Sicker; Ekkehard Stehfest; Horst Wilde; Pierre Martin


Publisher
John Wiley and Sons
Year
1996
Tongue
German
Weight
280 KB
Volume
79
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis


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.


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