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

doi:10.1016/S0040-4020(01)85638-6

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

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

74 Citations (Scopus)

Abstract

Intramolecular N-alkylation of D-glucose-derived substrate 21E proceeded in an S_N2′ 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 language	English
Pages (from-to)	5681-5704
Number of pages	24
Journal	Tetrahedron
Volume	50
Issue number	19
DOIs	https://doi.org/10.1016/S0040-4020(01)85638-6
Publication status	Published - 1994

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(01)85638-6

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

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.",

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

year = "1994",

doi = "10.1016/S0040-4020(01)85638-6",

language = "English",

volume = "50",

pages = "5681--5704",

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

T2 - palladium(O)-catalyzed intramolecular N-alkylation for the key piperidine ring formation

AU - Takao, Ken ichi

AU - Nigawara, Yuya

AU - Nishino, Emiko

AU - Takagi, Izumi

AU - Maeda, Koji

AU - Tadano, Kin ichi

AU - Ogawa, Seiichiro

PY - 1994

Y1 - 1994

N2 - 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.

AB - 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.

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U2 - 10.1016/S0040-4020(01)85638-6

DO - 10.1016/S0040-4020(01)85638-6

M3 - Article

AN - SCOPUS:0028260784

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VL - 50

SP - 5681

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JO - Tetrahedron

JF - Tetrahedron

IS - 19

ER -

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

Abstract

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