Treatment of allylic chloride 18E, derived from D-glucose, with NaH in the presence of a catalytic amount of Pd(Ph3P)4 provided a piperidine derivative 19 with high diastereoselectivity. Further functional group transformation from 19 completed enantiospecific total syntheses of (-)-desoxoprosopinine 3 and (-)-desoxoprosophylline 4.
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Tadano et al. (1993) studied this question.