Enantioselective synthesis of ()-(1R,2R)-1,2-dihydrochrysene-1,2-diol》.pdfVIP

Tetrahedron 70 (2014) 9041e9051 Contents lists available at ScienceDirect Tetrahedron journal homepage: www.elsevier.c om/locate/tet Enantioselective synthesis of ()-(1R,2R)-1,2-dihydrochrysene- 1,2-diol * Marianne Lorentzen, Magne O. Sydnes, Kare B. Jørgensen Department of Mathematic and Natural Science, Faculty of Science and Technology, University of Stavanger, N-4036 Stavanger, Norway a r t i c l e i n f o a b s t r a c t Article history: A general chiral building block containing the 1R,2R-trans-diol moiety was constructed utilizing the Received 5 August 2014 stereoselective Shi-epoxidation reaction on a tetralone scaffold assembled by a Negishi cross-coupling on Received in revised form 25 September 2014 N,N-diethylbenzamide. Further elaboration of this chiral building block into polycyclic aromatic com- Accepted 6 October 2014 pounds was demonstrated with the total synthesis of the precursor for the most carcinogenic metabolite Available online 13 October 2014 of chrysene, ()-(1R,2R)-1,2-dihydrochrysene-1,2-diol in 87% ee. 2014 Elsevier Ltd. All rights reserved. Keywords: Cross-coupling FriedeleCrafts acylation PAH-metabolites Shi-epoxidation trans-Dihydrodiol 1. Introduction