Stereoselective total syntheses of (-)-desoxoprosopinine and (-)-desoxoprosophylline: palladium(O)-catalyzed intramolecular N-alkylation for the key piperidine ring formation

Ken ichi Takao, Yuya Nigawara, Emiko Nishino, Izumi Takagi, Koji Maeda, Kin ichi Tadano, Seiichiro Ogawa

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69 Citations (Scopus)

Abstract

Intramolecular N-alkylation of D-glucose-derived substrate 21E proceeded in an SN2′ mode smoothly in the presence of a Pd(O)catalyst and n-Bu4NI. The major cyclization product, a 2,6-dialkylated piperidine 22t, was effectively converted into the title alkaloids.

Original languageEnglish
Pages (from-to)5681-5704
Number of pages24
JournalTetrahedron
Volume50
Issue number19
DOIs
Publication statusPublished - 1994

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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