Synthesis of a biologically active D-ring diolepoxide of the potent carcinogen 7,12-dimethylbenz[a]anthracene (2)†
✍ Scribed by Ronald G. Harvey; Peter P. Fu; Cecilia Cortez; John Pataki
- Publisher
- Elsevier Science
- Year
- 1977
- Tongue
- French
- Weight
- 207 KB
- Volume
- 18
- Category
- Article
- ISSN
- 0040-4039
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## Abstract The 2 + 4 cycloaddition reaction of 1,4‐naphthoquinone and substituted styrenes was used to prepare 1‐, 2‐, 3‐, and 4‐bromobenz[a]anthracene‐7,12‐diones (BADs). The corresponding bromobenz[a]anthracenes (BAs) were prepared by aluminum tricyclohexoxide reduction of the diones. Lithiation
Stereospecific syntheses of the anti-and syn-diol epoxides of 7-and 12-methylbenz[a]anthracene, suspected as active metabolites of the parent PAHs but previously thought to be too chemically reactive and unstable to isolate, are described and the pure compounds are shown to be moderately stable.