Total synthesis of the antipode of alkaloid 205 B

Naoki Toyooka; Ayako Fukutome; Hiroyuki Shinoda; Hideo Nemoto

doi:10.1002/anie.200351906

Total synthesis of the antipode of alkaloid 205 B

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

40 Scopus citations

Abstract

Forming the tetrasubstituted piperidine ring with stereocontrol in a Michael-type conjugate addition is a key step in the first enantioselective synthesis of the antipode 1 of alkaloid 205 B. The absolute stereo-chemistry of the natural product could be determined unambiguously by comparison of the optical rotations.

Original language	English
Pages (from-to)	3808-3810
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	42
Issue number	32
DOIs	https://doi.org/10.1002/anie.200351906
State	Published - 2003/08/18

Keywords

Alkaloids
Michael addition
Natural products
Nitrogen heterocycles
Stereoelectronic effects

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.200351906

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title = "Total synthesis of the antipode of alkaloid 205 B",

abstract = "Forming the tetrasubstituted piperidine ring with stereocontrol in a Michael-type conjugate addition is a key step in the first enantioselective synthesis of the antipode 1 of alkaloid 205 B. The absolute stereo-chemistry of the natural product could be determined unambiguously by comparison of the optical rotations.",

keywords = "Alkaloids, Michael addition, Natural products, Nitrogen heterocycles, Stereoelectronic effects",

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

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doi = "10.1002/anie.200351906",

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AU - Toyooka, Naoki

AU - Fukutome, Ayako

AU - Shinoda, Hiroyuki

AU - Nemoto, Hideo

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Y1 - 2003/8/18

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KW - Alkaloids

KW - Michael addition

KW - Natural products

KW - Nitrogen heterocycles

KW - Stereoelectronic effects

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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Total synthesis of the antipode of alkaloid 205 B

Abstract

Keywords

ASJC Scopus subject areas

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