Stereodivergent synthesis of the 2,3,5,6-tetrasubstituted piperidine ring system: An application to the synthesis of alkaloids

Naoki Toyooka; Ayako Fukutome; Hiroyuki Shinoda; Hideo Nemoto

doi:10.1016/j.tet.2004.05.039

Stereodivergent synthesis of the 2,3,5,6-tetrasubstituted piperidine ring system: An application to the synthesis of alkaloids

Naoki Toyooka^*, Ayako Fukutome, Hiroyuki Shinoda, Hideo Nemoto

^*Corresponding author for this work

Life Sciences and Bioengineering

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

30 Scopus citations

Abstract

Stereodivergent synthesis of the 2,3,5,6-tetrasubstituted piperidine ring system has been achieved by sequential stereocontrolled Michael-type conjugate addition reaction of appropriate enaminoesters. This methodology has been applied to the total syntheses of the poison frog alkaloids 223A and 205B. The relative stereochemistry of natural 223A at the 6-position was revised, and the absolute stereochemistry of natural 205B was determined by the present synthesis.

Original language	English
Pages (from-to)	6197-6216
Number of pages	20
Journal	Tetrahedron
Volume	60
Issue number	29
DOIs	https://doi.org/10.1016/j.tet.2004.05.039
State	Published - 2004/07/12

Keywords

Alkaloids
Comins' triflating agent
Piperidones

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2004.05.039

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title = "Stereodivergent synthesis of the 2,3,5,6-tetrasubstituted piperidine ring system: An application to the synthesis of alkaloids",

abstract = "Stereodivergent synthesis of the 2,3,5,6-tetrasubstituted piperidine ring system has been achieved by sequential stereocontrolled Michael-type conjugate addition reaction of appropriate enaminoesters. This methodology has been applied to the total syntheses of the poison frog alkaloids 223A and 205B. The relative stereochemistry of natural 223A at the 6-position was revised, and the absolute stereochemistry of natural 205B was determined by the present synthesis.",

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author = "Naoki Toyooka and Ayako Fukutome and Hiroyuki Shinoda and Hideo Nemoto",

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T1 - Stereodivergent synthesis of the 2,3,5,6-tetrasubstituted piperidine ring system

T2 - An application to the synthesis of alkaloids

AU - Toyooka, Naoki

AU - Fukutome, Ayako

AU - Shinoda, Hiroyuki

AU - Nemoto, Hideo

PY - 2004/7/12

Y1 - 2004/7/12

N2 - Stereodivergent synthesis of the 2,3,5,6-tetrasubstituted piperidine ring system has been achieved by sequential stereocontrolled Michael-type conjugate addition reaction of appropriate enaminoesters. This methodology has been applied to the total syntheses of the poison frog alkaloids 223A and 205B. The relative stereochemistry of natural 223A at the 6-position was revised, and the absolute stereochemistry of natural 205B was determined by the present synthesis.

AB - Stereodivergent synthesis of the 2,3,5,6-tetrasubstituted piperidine ring system has been achieved by sequential stereocontrolled Michael-type conjugate addition reaction of appropriate enaminoesters. This methodology has been applied to the total syntheses of the poison frog alkaloids 223A and 205B. The relative stereochemistry of natural 223A at the 6-position was revised, and the absolute stereochemistry of natural 205B was determined by the present synthesis.

KW - Alkaloids

KW - Comins' triflating agent

KW - Piperidones

UR - http://www.scopus.com/inward/record.url?scp=3042656762&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2004.05.039

DO - 10.1016/j.tet.2004.05.039

M3 - 学術論文

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SN - 0040-4020

VL - 60

SP - 6197

EP - 6216

JO - Tetrahedron

JF - Tetrahedron

IS - 29

ER -

Stereodivergent synthesis of the 2,3,5,6-tetrasubstituted piperidine ring system: An application to the synthesis of alkaloids

Abstract

Keywords

ASJC Scopus subject areas

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