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

doi:10.1055/s-1993-22530

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

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	565-567
Number of pages	3
Journal	Synlett
Volume	1993
Issue number	8
DOIs	https://doi.org/10.1055/s-1993-22530
Publication status	Published - 1993 Aug

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-1993-22530

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title = "Stereoselective total syntheses of (-)-desoxoprosopinine and (-)-desoxoprosophylline: Palladium(0)-catalyzed intramolecular n-alkylation for the key piperidine ring formation",

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. ",

author = "Tadano, {Kin Ichi} and Takao, {Ken Ichi} and Yuya Nigawara and Emiko Nishino and Izumi Takagi and Koji Maeda and Seiichiro Ogawa",

year = "1993",

month = aug,

doi = "10.1055/s-1993-22530",

language = "English",

volume = "1993",

pages = "565--567",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

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T1 - Stereoselective total syntheses of (-)-desoxoprosopinine and (-)-desoxoprosophylline

T2 - Palladium(0)-catalyzed intramolecular n-alkylation for the key piperidine ring formation

AU - Tadano, Kin Ichi

AU - Takao, Ken Ichi

AU - Nigawara, Yuya

AU - Nishino, Emiko

AU - Takagi, Izumi

AU - Maeda, Koji

AU - Ogawa, Seiichiro

PY - 1993/8

Y1 - 1993/8

N2 - 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.

AB - 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.

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U2 - 10.1055/s-1993-22530

DO - 10.1055/s-1993-22530

M3 - Article

AN - SCOPUS:0002880101

SN - 0936-5214

VL - 1993

SP - 565

EP - 567

JO - Synlett

JF - Synlett

IS - 8

ER -

Stereoselective total syntheses of (-)-desoxoprosopinine and (-)-desoxoprosophylline: Palladium(0)-catalyzed intramolecular n-alkylation for the key piperidine ring formation

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