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Total synthesis of streptonigrone.
J Org Chem
October 2007
Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, Canada BC V6T 1Z1.
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.
View Article and Find Full Text PDFTransformation of streptonigrin into streptonigrone; synthesis and biological evaluation of antibiotics streptonigrin and streptonigrone alkyl ethers.
J Antibiot (Tokyo)
February 1992
Institute of New Antibiotics, USSR Academy of Medical Sciences, Moscow.
A method of synthesis of antibiotic streptonigrin 8'-O-alkyl ethers by alkylation of streptonigrin diphenylmethyl ester and consequent deprotection of carboxylic group with CF3COOH is developed. An attempt to deblock carboxylic group of 8'-O-methylstreptonigrin diphenylmethyl ester by hydrogenation over Pd produced 8'-O-methylstreptonigrone. Similarly streptonigrin was transformed into streptonigrone over Pd-black in H2 stream.
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