Issue 23, 1975
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Absolute stereochemistry of the dihydroanthracene-cis- and trans-1,2-diols produced from anthracene by mammals and bacteria

M. Naseem Akhtar,   Derek R. Boyd,   Norris J. Thompson,   Masato Koreeda,   David T. Gibson,   Venkatanarayana Mahadevan  and  Donald M. Jerina  

Abstract

(+)-1,2-Dihydroanthracene-trans- and -cis-1,2-diols have been isolated as major anthracene metabolites from rabbits and the bacterium Beijerinckia B-836, respectively. The absolute stereochemistry and optical purity of each diol has been related to that of 1,2,3,4-tetrahydroanthracen-2-ol. The latter was resolved via the diastereoisomeric (–)-methyloxyacetates, whose optical purity and absolute stereochemistry was determined by a range of techniques including kinetic resolution, asymmetric synthesis, and c.d. (exciton chirality method).

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Article information

DOI
https://doi.org/10.1039/P19750002506
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1975, 2506-2511

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Absolute stereochemistry of the dihydroanthracene-cis- and trans-1,2-diols produced from anthracene by mammals and bacteria

M. N. Akhtar, D. R. Boyd, N. J. Thompson, M. Koreeda, D. T. Gibson, V. Mahadevan and D. M. Jerina, J. Chem. Soc., Perkin Trans. 1, 1975, 2506 DOI: 10.1039/P19750002506

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