Structure and Synthesis of Kotanin and Desmethylkotanin, Metabolites of Aspergillus glaucus

G. Büchi, Dieter H. Klaubert, Steven M. Weinreb, K. C. Shank, G. N. Wogan, G. Büchi, Dieter H. Klaubert, Steven M. Weinreb, K. C. Shank, G. N. Wogan

Research output: Contribution to journalArticle

55 Citations (Scopus)

Abstract

Two new metabolites, for which the names kotanin and desmethylkotanin are suggested, have been isolated from Aspergillus glaucus cultures. Spectral data on the metabolites and their base hydrolysis products were used to derive structures which were confirmed by total synthesis of racemic kotanin. Oxidative coupling of organocuprates served in the synthesis of various biphenyls. Neither of the two metabolites seems to be responsible for the toxicity of the total A. glaucus extracts.

Original languageEnglish (US)
Pages (from-to)1143-1147
Number of pages5
JournalJournal of Organic Chemistry
Volume36
Issue number8
DOIs
StatePublished - Apr 1 1971

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Aspergillus
Metabolites
Toxicity
Hydrolysis
kotanin

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Büchi, G., Klaubert, D. H., Weinreb, S. M., Shank, K. C., Wogan, G. N., Büchi, G., ... Wogan, G. N. (1971). Structure and Synthesis of Kotanin and Desmethylkotanin, Metabolites of Aspergillus glaucus. Journal of Organic Chemistry, 36(8), 1143-1147. https://doi.org/10.1021/jo00807a028
Büchi, G. ; Klaubert, Dieter H. ; Weinreb, Steven M. ; Shank, K. C. ; Wogan, G. N. ; Büchi, G. ; Klaubert, Dieter H. ; Weinreb, Steven M. ; Shank, K. C. ; Wogan, G. N. / Structure and Synthesis of Kotanin and Desmethylkotanin, Metabolites of Aspergillus glaucus. In: Journal of Organic Chemistry. 1971 ; Vol. 36, No. 8. pp. 1143-1147.
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Büchi, G, Klaubert, DH, Weinreb, SM, Shank, KC, Wogan, GN, Büchi, G, Klaubert, DH, Weinreb, SM, Shank, KC & Wogan, GN 1971, 'Structure and Synthesis of Kotanin and Desmethylkotanin, Metabolites of Aspergillus glaucus', Journal of Organic Chemistry, vol. 36, no. 8, pp. 1143-1147. https://doi.org/10.1021/jo00807a028

Structure and Synthesis of Kotanin and Desmethylkotanin, Metabolites of Aspergillus glaucus. / Büchi, G.; Klaubert, Dieter H.; Weinreb, Steven M.; Shank, K. C.; Wogan, G. N.; Büchi, G.; Klaubert, Dieter H.; Weinreb, Steven M.; Shank, K. C.; Wogan, G. N.

In: Journal of Organic Chemistry, Vol. 36, No. 8, 01.04.1971, p. 1143-1147.

Research output: Contribution to journalArticle

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Büchi G, Klaubert DH, Weinreb SM, Shank KC, Wogan GN, Büchi G et al. Structure and Synthesis of Kotanin and Desmethylkotanin, Metabolites of Aspergillus glaucus. Journal of Organic Chemistry. 1971 Apr 1;36(8):1143-1147. https://doi.org/10.1021/jo00807a028