Efficient construction of the core framework of lysidicin A via three Claisen rearrangements including a cascade reaction

Yusuke Ogura; Hidenori Watanabe

doi:10.1016/j.tetlet.2010.04.073

Efficient construction of the core framework of lysidicin A via three Claisen rearrangements including a cascade reaction

Yusuke Ogura, Hidenori Watanabe

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

2 Citations (Scopus)

Abstract

A model compound (6) with the core skeleton of lysidicin A was synthesized as a racemate. The key step (8→7) includes three Claisen rearrangements of the triether with phloroglucinols; two of which rearranged in a cascade manner and the other was a simple rearrangement. This one-pot reaction enabled the introduction of three phloroglucinol units at the correct positions and makes the synthetic approach significantly efficient.

Original language	English
Pages (from-to)	3294-3296
Number of pages	3
Journal	Tetrahedron Letters
Volume	51
Issue number	25
DOIs	https://doi.org/10.1016/j.tetlet.2010.04.073
Publication status	Published - 2010 Jun 23
Externally published	Yes

Keywords

Cascade reaction
Claisen rearrangement
Lysidicin A
Vasodilation activity

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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keywords = "Cascade reaction, Claisen rearrangement, Lysidicin A, Vasodilation activity",

author = "Yusuke Ogura and Hidenori Watanabe",

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AU - Ogura, Yusuke

AU - Watanabe, Hidenori

PY - 2010/6/23

Y1 - 2010/6/23

N2 - A model compound (6) with the core skeleton of lysidicin A was synthesized as a racemate. The key step (8→7) includes three Claisen rearrangements of the triether with phloroglucinols; two of which rearranged in a cascade manner and the other was a simple rearrangement. This one-pot reaction enabled the introduction of three phloroglucinol units at the correct positions and makes the synthetic approach significantly efficient.

AB - A model compound (6) with the core skeleton of lysidicin A was synthesized as a racemate. The key step (8→7) includes three Claisen rearrangements of the triether with phloroglucinols; two of which rearranged in a cascade manner and the other was a simple rearrangement. This one-pot reaction enabled the introduction of three phloroglucinol units at the correct positions and makes the synthetic approach significantly efficient.

KW - Cascade reaction

KW - Claisen rearrangement

KW - Lysidicin A

KW - Vasodilation activity

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SN - 0040-4039

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Efficient construction of the core framework of lysidicin A via three Claisen rearrangements including a cascade reaction

Abstract

Keywords

ASJC Scopus subject areas

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