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
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
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DOI：
10.1021/jo0303822
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发表时间：
2004-05-28
影响因子：
3.6
通讯作者：
Amin, S
中科院分区：
文献类型：
--
作者：
Sharma, AK;Kumar, S;Amin, S
二苯并[def，p]芘（DBC）（1）是迄今为止发现的最具致突变性和毒性的多环芳烃。其代谢活化产生反式-11，12-二羟基-11，12-二氢-DBC（2），后者进一步代谢为最终代谢产物抗-反式-11，12-二羟基-13，14-环氧-11，12，13，14-四氢-DBC（3），后者与DNA结合，导致突变并最终诱导肿瘤。本文报道了一种简便的合成DBC（1）及其12-甲氧基衍生物（12-methoxy-DBC）（13）的方法，该方法采用Suzuki交叉偶联法，是合成2和3的关键中间体。
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-dihydroxv-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.