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Synlett 1993; 1993(8): 565-567
DOI: 10.1055/s-1993-22530
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Stereoselective Total Syntheses of (-)-Desoxoprosopinine and (-)-Desoxoprosophylline: Palladium(0)-Catalyzed Intramolecular N-Alkylation for the Key Piperidine Ring Formation

Kin-ichi Tadano* , Ken-ichi Takao, Yuya Nigawara, Emiko Nishino, Izumi Takagi, Koji Maeda, Seiichiro Ogawa
  • *Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223, Japan
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Publication Date:
19 March 2002 (online)

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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.