Transformation Products from Lycoctonine

Transformation Products from Lycoctonine. - Edwards has reported an unexpected rearrangement during deamination of 4-amino-4-des(oxy-methylene)-anhydrolycoctonam (117). In studies of the chemistry of lycoctonine (3), treatment of its derivative lycoctonamic acid (118) with very dilute sulfuric acid afforded the pinacolic dehydration product (119). This acid was converted to (117) by Curtius or Hofmann degradation. When (117) was treated with nitrous acid, the hydroxyketolactam (120) and the aldehydolactam acid (121) were obtained as the main products in 50 and 20% yields, respectively. 

Since difficulties were encountered in the interpretation of other chemical and spectral evidence, these structures were assigned on the basis of crystallographic analyses of derivatives. Reduc- 

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