Stereoselective total syntheses of (-)-desoxoprosopinine and (-)-desoxoprosophylline

palladium(O)-catalyzed intramolecular N-alkylation for the key piperidine ring formation

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

Research output: Contribution to journalArticle

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

Fingerprint

Cyclization
Alkylation
Palladium
Alkaloids
Glucose
Catalysts
Substrates
piperidine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Stereoselective total syntheses of (-)-desoxoprosopinine and (-)-desoxoprosophylline : palladium(O)-catalyzed intramolecular N-alkylation for the key piperidine ring formation. / Takao, Kenichi; Nigawara, Yuya; Nishino, Emiko; Takagi, Izumi; Maeda, Koji; Tadano, Kin ichi; Ogawa, Seiichiro.

In: Tetrahedron, Vol. 50, No. 19, 1994, p. 5681-5704.

Research output: Contribution to journalArticle

Takao, Kenichi ; Nigawara, Yuya ; Nishino, Emiko ; Takagi, Izumi ; Maeda, Koji ; Tadano, Kin ichi ; Ogawa, Seiichiro. / Stereoselective total syntheses of (-)-desoxoprosopinine and (-)-desoxoprosophylline : palladium(O)-catalyzed intramolecular N-alkylation for the key piperidine ring formation. In: Tetrahedron. 1994 ; Vol. 50, No. 19. pp. 5681-5704.
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