Synthesis of (±)-Lasubine II Using N-Methoxyamines

Takashi Yokoyama; Yutaro Fukami; Takaaki Sato; Noritaka Chida

doi:10.1002/asia.201501143

Synthesis of (±)-Lasubine II Using N-Methoxyamines

Takashi Yokoyama, Yutaro Fukami, Takaaki Sato, Noritaka Chida

Department of Applied Chemistry

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

9 Citations (Scopus)

Abstract

The synthesis of (±)-lasubine II has been achieved through a three-component allylation capitalizing on the unique properties of N-methoxyamines. This reaction enabled the installation of all the carbon atoms of lasubine¯II in a single operation. The N-methoxy group was efficiently used for the subsequent nitrone formation. A single-step cyclization of isoxazolidines or N-methoxyamines to form functionalized piperidine rings was also developed.

Original language	English
Pages (from-to)	470-473
Number of pages	4
Journal	Chemistry - An Asian Journal
Volume	11
Issue number	4
DOIs	https://doi.org/10.1002/asia.201501143
Publication status	Published - 2016 Feb 18

Keywords

allylation
amines
lasubine
multicomponent reactions
total synthesis

ASJC Scopus subject areas

Chemistry(all)
Biochemistry
Organic Chemistry

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10.1002/asia.201501143

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title = "Synthesis of (±)-Lasubine II Using N-Methoxyamines",

abstract = "The synthesis of (±)-lasubine II has been achieved through a three-component allylation capitalizing on the unique properties of N-methoxyamines. This reaction enabled the installation of all the carbon atoms of lasubine¯II in a single operation. The N-methoxy group was efficiently used for the subsequent nitrone formation. A single-step cyclization of isoxazolidines or N-methoxyamines to form functionalized piperidine rings was also developed.",

keywords = "allylation, amines, lasubine, multicomponent reactions, total synthesis",

author = "Takashi Yokoyama and Yutaro Fukami and Takaaki Sato and Noritaka Chida",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

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AU - Yokoyama, Takashi

AU - Fukami, Yutaro

AU - Sato, Takaaki

AU - Chida, Noritaka

PY - 2016/2/18

Y1 - 2016/2/18

N2 - The synthesis of (±)-lasubine II has been achieved through a three-component allylation capitalizing on the unique properties of N-methoxyamines. This reaction enabled the installation of all the carbon atoms of lasubine¯II in a single operation. The N-methoxy group was efficiently used for the subsequent nitrone formation. A single-step cyclization of isoxazolidines or N-methoxyamines to form functionalized piperidine rings was also developed.

AB - The synthesis of (±)-lasubine II has been achieved through a three-component allylation capitalizing on the unique properties of N-methoxyamines. This reaction enabled the installation of all the carbon atoms of lasubine¯II in a single operation. The N-methoxy group was efficiently used for the subsequent nitrone formation. A single-step cyclization of isoxazolidines or N-methoxyamines to form functionalized piperidine rings was also developed.

KW - allylation

KW - amines

KW - lasubine

KW - multicomponent reactions

KW - total synthesis

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JO - Chemistry - An Asian Journal

JF - Chemistry - An Asian Journal

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ER -

Synthesis of (±)-Lasubine II Using N-Methoxyamines

Abstract

Keywords

ASJC Scopus subject areas

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