Total synthesis of streptonigrone.
A total synthesis of streptonigrone, 1, is described, which incorporates a one-step synthesis of substituted pyridones devised in our laboratory. Other aspects of the synthesis that differentiate the present approach from previous ones are the use of a Conrad-Limpach reaction, rather than the customary Friedländer methodology, to assemble the quinoline segment of 1, and the implementation of an anionic sequence for the functionalization of a key pyridone intermediate.
Chan
Bryan K
BK
Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, Canada BC V6T 1Z1.
Ciufolini
Marco A
MA
D015394:Molecular Structure; D013237:Stereoisomerism; D013308:Streptonigrin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D013308:Streptonigrin; C045696:streptonigrone