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

Palladium(0)-catalyzed intramolecular n-alkylation for the key piperidine ring formation

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

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Treatment of allylic chloride 18E, derived from D-glucose, with NaH in the presence of a catalytic amount of Pd(Ph 3 P) 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.

Original languageEnglish
Pages (from-to)565-567
Number of pages3
JournalSynlett
Volume1993
Issue number8
DOIs
Publication statusPublished - 1993 Aug 1

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Alkylation
Palladium
Functional groups
Chlorides
Derivatives
Glucose
piperidine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Stereoselective total syntheses of (-)-desoxoprosopinine and (-)-desoxoprosophylline : Palladium(0)-catalyzed intramolecular n-alkylation for the key piperidine ring formation. / Tadano, Kin Ichi; Takao, Kenichi; Nigawara, Yuya; Nishino, Emiko; Takagi, Izumi; Maeda, Koji; Ogawa, Seiichiro.

In: Synlett, Vol. 1993, No. 8, 01.08.1993, p. 565-567.

Research output: Contribution to journalArticle

Tadano, Kin Ichi ; Takao, Kenichi ; Nigawara, Yuya ; Nishino, Emiko ; Takagi, Izumi ; Maeda, Koji ; Ogawa, Seiichiro. / Stereoselective total syntheses of (-)-desoxoprosopinine and (-)-desoxoprosophylline : Palladium(0)-catalyzed intramolecular n-alkylation for the key piperidine ring formation. In: Synlett. 1993 ; Vol. 1993, No. 8. pp. 565-567.
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AU - Takao, Kenichi

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AU - Takagi, Izumi

AU - Maeda, Koji

AU - Ogawa, Seiichiro

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