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

doi:10.1021/jo00807a028

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

Chemistry

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63 Scopus citations

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 language	English (US)
Pages (from-to)	1143-1147
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	36
Issue number	8
DOIs	https://doi.org/10.1021/jo00807a028
State	Published - Apr 1 1971

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo00807a028

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title = "Structure and Synthesis of Kotanin and Desmethylkotanin, Metabolites of Aspergillus glaucus",

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.",

author = "G. B{\"u}chi and Klaubert, {Dieter H.} and Weinreb, {Steven M.} and Shank, {K. C.} and Wogan, {G. N.} and G. B{\"u}chi and Klaubert, {Dieter H.} and Weinreb, {Steven M.} and Shank, {K. C.} and Wogan, {G. N.}",

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T1 - Structure and Synthesis of Kotanin and Desmethylkotanin, Metabolites of Aspergillus glaucus

AU - Büchi, G.

AU - Klaubert, Dieter H.

AU - Weinreb, Steven M.

AU - Shank, K. C.

AU - Wogan, G. N.

AU - Büchi, G.

AU - Klaubert, Dieter H.

AU - Weinreb, Steven M.

AU - Shank, K. C.

AU - Wogan, G. N.

PY - 1971/4/1

Y1 - 1971/4/1

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AB - 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.

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ER -

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

Abstract

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