Journal
TETRAHEDRON
Volume 70, Issue 47, Pages 9041-9051Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.10.016
Keywords
Cross-coupling; Friedel-Crafts acylation; PAH-metabolites; Shi-epoxidation; trans-Dihydrodiol
Categories
Funding
- University of Stavanger
- research program Green Production Chemistry
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A general chiral building block containing the 1R,2R-trans-diol moiety was constructed utilizing the stereoselective Shi-epoxidation reaction on a tetralone scaffold assembled by a Negishi cross-coupling on N,N-diethylbenzamide. Further elaboration of this chiral building block into polycyclic aromatic compounds was demonstrated with the total synthesis of the precursor for the most carcinogenic metabolite of chrysene, (-)-(1R,2R)-1,2-dihydrochrysene-1,2-diol in 87% ee. (C) 2014 Elsevier Ltd. All rights reserved.
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