A novel regio- and stereocontrolled synthesis of diol epoxide and trans-dihydrodiol metabolites of polycyclic aromatic hydrocarbons. An application to the synthesis of the bay-region syn- and anti-diol epoxides of the carcinogen 1,4-dimethylphenanthrene

Journal Article · Wed Sep 26 04:00:00 EDT 1990 · Journal of the American Chemical Society; (United States)

DOI:https://doi.org/10.1021/ja00176a062· OSTI ID:5406449

Koreeda, Masato; Jung, Keeyong; Hirota, Mitsuru ^[1]

---

1. Univ. of Michigan, Ann Arbor (USA)

Carcinogenic polycyclic aromatic hydrocarbons (PAHs) require metabolic activation in order to exert their tumorigenic activity, typically to the diol epoxides as predicted by the bay-region concept. While a number of synthetic methods toward these diol epoxides are described in the literature, it was felt that a new, entirely different approach may be needed that achieves regio- and stereochemically controlled synthesis of these metabolites, particularly the bay-region analogues. The authors delineate a generally applicable, efficient synthesis of PAH diol epoxides and trans-dihydrodiols and its application to the first synthesis of the putative active metabolites, the bay-region diol epoxides of the carcinogen 1,4-dimethylphenanthrene (1,4-DMPh).

• OSTI ID: 5406449
• Journal Information: Journal of the American Chemical Society; (United States), Journal Name: Journal of the American Chemical Society; (United States) Vol. 112:20; ISSN 0002-7863; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
560300 -- Chemicals Metabolism & Toxicology
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
AROMATICS
CARCINOGENS
CHEMICAL PREPARATION
CONDENSED AROMATICS
EPOXIDES
HYDROCARBONS
METABOLITES
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PHENANTHRENE
POLYCYCLIC AROMATIC HYDROCARBONS
STEREOCHEMISTRY
SYNTHESIS