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■ Improved Labelling Methods for C9-²H-Retronecine

Jeannette T. Hovermale, Fraser F. Fleming, James D. White, and A. Morrie Craig*

*College of Veterinary Medicine, Oregon State University, Gilbert Hall 153, Corvallis Oregon 97331, U.S.A.

Abstract

The necine base retronecine (1a), common to numerous toxic pyrrolizidine alkaloids, has previously been labelled with ³H at C-9 for use in metabolic studies. The current method for labelling retronecine is inefficient, and we report here an improved method of which utilizes the Dess-Martin periodinane reagent. Characterization of the resulting aldehyde (2) is described. The overall yield of C9-²H-retronecine (1b) is 71% (from 1a).