Enantioselective synthesis of (-)-(1R,2R)-1,2-dihydrochrysene-1,2-diol
Peer reviewed, Journal article
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Original versionLorentzen, M., Sydnes, M.O., Jørgensen, K.B. (2014) Enantioselective synthesis of (-)-(1R,2R)-1,2-dihydrochrysene-1,2-diol. Tetrahedron, 70 (47), pp. 9041-9051. 10.1016/j.tet.2014.10.016
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.