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

Research output: Contribution to journalArticlepeer-review

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

ASJC Scopus subject areas

  • Organic Chemistry

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