Studies on Metabolites of Macrophoma commelinae. IV. Substrate Specificity in the Biotransformation of 2-Pyrones to Substituted Benzoic Acids
Substrate specificity in the novel biotransformation from 2-pyrone derivatives to substituted benzoic acids by Macrophoma commelinae (IFO 9570) was investigated by means of feeding experiments with various compounds.Among them, 2-pyrone derivatives substituted by an electron-donating group at C-4, by an electron-withdrawing group at C-5 and by an alkyl group at C-6 were converted to the corresponding benzoic acid derivatives in fairly good yields.The C3-unit precursors and intermediates were examined in stationary or shaking culture.Based on the experimental results obtained, a mechanism for this unique reaction is proposed. macrophoma commelinae IFO 9570; fungi; 2-pyrone; substituted benzoic acid; biotransformation; substrate specificity; aromatic ring formation; macrophomic acid
SYNTHESIS OF PYRENOCINES A, B AND PYRENOCHAETIC ACID A
Starting from 5-acetyl-4-hydroxy-6-methyl-α-pyrone, three phytotoxins, pyrenocines A, B and pyrenochaetic acid A were synthesized.Retro-Diels-Alder reaction was successfully applied in the synthesis of pyrenochaetic acid A.
Ichihara, Akitami,Murakami, Kazuo,Sakamura, Sadao
p. 5245 - 5250
(2007/10/02)
SYNTHESIS OF PYRENOCINE A AND B
From 5-acetyl-4-hydroxy-6-methyl-α-pyrone, two phytotoxins, pyrenocine A and B, were synthesised and erroneous γ-pyrone structure of the starting compound was corrected on the basis of spectroscopic data.
Ichihara, Akitami,Murakami, Kazuo,Sakamura, Sadao
p. 4005 - 4006
(2007/10/02)
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