Synthesis and assignment of absolute configuration to the trans 3,4-dihydrodiols and 3,4-diol-1,2-epoxides of benzo[c]phenanthrene
โ Scribed by H. Yagi; D.R. Thakker; Y. Ittah; M. Croisy-Delcey; D.M. Jerina
- Publisher
- Elsevier Science
- Year
- 1983
- Tongue
- French
- Weight
- 278 KB
- Volume
- 24
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
The (+)-and (-)-trans-3,4-dihydroxy-3,4-dihydrobenzo[c]phenanthrenes have been resolved and assigned absolute configuration by independent nmr and CD methods. Each was converted to its pair of diastereomeric bay-region 3,4-diol-1,2-epoxides in which the benzylic 4-hydroxyl group is either cis or trans to the epoxide oxygen. Benzo[c]phenanthrene is a widespread environmental pollutant la with weak tumorigenic activity on mouse skin. lb In accord with predictions of the bay-region theory, 2 its diastereomerit 3,4-diol-1,2-epoxides derived from the trans 3,4-dihydrodiol have been shown to possess
๐ SIMILAR VOLUMES
Racemic anti-benzo[c]phenanthrene-3,4-diol-I ,2-epoxide (BcPDE) is a powerful rat mammary carcinogen and a metabolite of benzo[c]phenanthrene, a polynuclear aromatic hydrocarbon found in the environment. In elucidating potential molecular mechanisms that may play a role in the development of BcPDE-i