Concisely synthesizing dibenzo[def,p]chrysene and its 13C2-labeled analog, a high potent carcinogen implicated in causation of lung cancer in cigarette smokers

ORGN 410

Daiwang Xu, xdw@uchicago.edu1, Yazhen Duan1, and Ronald G. Harvey2. (1) Ben May department for Cancer Research, university of chicago, 929 E, 57th street, chicago, IL 60637, (2) Ben May departmemt for Cancer Research, University of Chicago, 929 E 57th street, Chicago, IL 60637
Dibenzo[def,p]chrysense (DBC) is the most potent polycyclic aromatic hydrocarbon carcinogen currently known. In connection with studies of elucidation of the role of DBC in human cancer, 13C-labeled analogues of DBC and its active metabolites were required. Here, a new, more convenient synthesis of DBC that is readily adaptable to the synthesis of 13C-labeled analogues of DBC (with two or more 13C-atoms) was reported. Appropriate modification of this method also provides convenient synthetic access to the active metabolites of DBC, Such as DBC 11,12-dihydrodiol, DBC 11,12-dione and DBC 11,12-diol-13,14-epoxide and their 13C-labeled analogues.

 

Heterocycles and Aromatics, Molecular Recognition and Self Assembly
8:00 PM-10:00 PM, Tuesday, April 8, 2008 Morial Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008