TY - JOUR
T1 - A highly abbreviated synthesis of dibenzo[def,p]chrysene and its 12-methoxy derivative, a key precursor for the synthesis of the proximate and ultimate carcinogens of dibenzo[def,p]chrysene
AU - Sharma, Arun K.
AU - Kumar, Subodh
AU - Amin, Shantu
PY - 2004/5/28
Y1 - 2004/5/28
N2 - Dibenzo[def,p]chrysene (DBC) (1), is by far the most mutagenic and toxic polycyclic aromatic hydrocarbon identified. Its metabolic activation leads to trans-11,12-dihydroxy-11,12-dihydro-DBC (2), which is further metabolized to the ultimate metabolite, anti-trans-11,12-dihydroxy-13,14-epoxy-11,12,13,14-tetrahydro-DBC (3), that binds to DNA causing mutations and ultimately tumor induction. We report a facile route for the syntheses of DBC (1) and its 12-methoxy derivative (12-methoxy-DBC) (13), a key intermediate for the synthesis of 2 and 3, using a Suzuki cross-coupling approach.
AB - Dibenzo[def,p]chrysene (DBC) (1), is by far the most mutagenic and toxic polycyclic aromatic hydrocarbon identified. Its metabolic activation leads to trans-11,12-dihydroxy-11,12-dihydro-DBC (2), which is further metabolized to the ultimate metabolite, anti-trans-11,12-dihydroxy-13,14-epoxy-11,12,13,14-tetrahydro-DBC (3), that binds to DNA causing mutations and ultimately tumor induction. We report a facile route for the syntheses of DBC (1) and its 12-methoxy derivative (12-methoxy-DBC) (13), a key intermediate for the synthesis of 2 and 3, using a Suzuki cross-coupling approach.
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U2 - 10.1021/jo0303822
DO - 10.1021/jo0303822
M3 - Article
C2 - 15153038
AN - SCOPUS:2442665320
SN - 0022-3263
VL - 69
SP - 3979
EP - 3982
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 11
ER -