The synthesis of 10-fluorobenzo[a]pyrene

✍ Scribed by Melvin S. Newman; Vinod K. Khanna

• Book ID: 101760079
• Publisher: Wiley (John Wiley & Sons)
• Year: 2010
• Weight: 162 KB
• Volume: 88
• Category: Article
• ISSN: 0037-9646
• DOI: 10.1002/bscb.19790881106

✦ Synopsis

Abstract

The synthesis of 10‐fluorobenzo[a]pyrene in four steps from 11‐fluoro‐12‐methylbenz[a]anthracene is described.

A current hypothesis concerning the metabolism which is responsible for the carcinogenic activity of benzo[a]pyrene, BP, maintains that BP is converted into isomers of 7,8‐dihydroxy‐9,10‐epoxy‐7,8,9, 10‐tetrahydrobenzo[a]pyrene which are the true carcinogens.^1^ If any of 7‐,8‐,9‐, and 10‐fluorobenzo[a]pyrenes proved carcinogenic an alternate mechanism for carcinogenesis would be required. If all four fluorinated compounds were non‐carcinogenic strong support of the current hypothesis would be provided.^2^ Accordingly we planned to synthesize the fluoro BP compounds so that adequate testing could be carried out.