C. Csutoras et al., SYNTHESES AND TRANSFORMATIONS OF NOVEL NITROGEN AND SULFUR-CONTAININGMORPHINANEDIENES, Monatshefte fuer Chemie, 128(12), 1997, pp. 1267-1273
The synthesis of 6-azido-6-demethoxythebaine (10) has been performed s
tarting from thebaine (1). Compound 10 undergoes a cycloaddition react
ion with the azadienophile PTAD to form bridgehead azide 14. The acid
catalyzed rearrangement of isothiocyanato diene 11 obtained from azido
diene 10 and thiocyanato dienes 8 and 9 leads to sulfur containing de
rivatives of apocodeine (17-20).