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

被引：8
|
作者：
Lorentzen, Marianne [1 ]
Sydnes, Magne O. [1 ]
Jorgensen, Kare B. [1 ]
机构：
[1] Univ Stavanger, Fac Sci & Technol, Dept Math & Nat Sci, N-4036 Stavanger, Norway
来源：
TETRAHEDRON | 2014年 / 70卷 / 47期
关键词：
Cross-coupling; Friedel-Crafts acylation; PAH-metabolites; Shi-epoxidation; trans-Dihydrodiol; POLYCYCLIC AROMATIC-HYDROCARBONS; PALLADIUM-CATALYZED REACTION; DIRECTED ORTHO-METALATION; DIOL-EPOXIDES; CHRYSENE 1,2-DIHYDRODIOL; ASYMMETRIC EPOXIDATION; METABOLIC-ACTIVATION; PROTEIN ADDUCTS; TERTIARY AMIDES; ARENE OXIDES;
D O I：
10.1016/j.tet.2014.10.016
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：9041 / 9051
页数：11
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