Allylic substitution/rearrangement of cannabinoids with trimethylsilyl bromide

✍ Scribed by Herbert H. Seltzman; M.Anthony Moody; Mosammat K. Begum

• Book ID: 104225430
• Publisher: Elsevier Science
• Year: 1992
• Tongue: French
• Weight: 183 KB
• Volume: 33
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)92658-3

✦ Synopsis

Trimethylsilyl bromide (TMSBr) in the presence of catalytic ZnZ2 induces facile substitution of allylic acetates to the bromides with or without rearrangement as governed by product stability. This was applied to the preparation of a key intermediate employed in the synthesis of important cannabinoid metabolites.

The synthesis of metabolites of A9-tetrahydrocannabinol, the active constituent of sarihuana, continues to be of interest.l-4 Of special interest is the synthesis of the urinary metabolite 9-carboxy-11-nor-A9-THC which, as the analyte assayed for in drug abuse testing for marihuana use, is sought as the analytical standard in forensic testing. The method most frequently used to prepare the carboxy metabolite utilizes