Formal synthesis of (-)-agelastatin A: An iron(II)-mediated cyclization strategy

Daisuke Shigeoka; Takuma Kamon; Takehiko Yoshimitsu

doi:10.3762/bjoc.9.99

Formal synthesis of (-)-agelastatin A: An iron(II)-mediated cyclization strategy

Daisuke Shigeoka, Takuma Kamon, Takehiko Yoshimitsu

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

19 Citations (Scopus)

Abstract

An iron(II)-mediated aminohalogenation of a cyclopentenyl N-tosyloxycarbamate provided new access to the key intermediate for the synthesis of (-)-agelastatin A (AA, 1), a potent antiproliferative alkaloid. The present synthetic endeavour offered an insight into the mechanism underlying the iron(II)-mediated aminohalogenation of N-tosyloxycarbamate, in which the radical properties of the N-iron intermediates in the redox states were operative.

Original language	English
Pages (from-to)	860-865
Number of pages	6
Journal	Beilstein Journal of Organic Chemistry
Volume	9
DOIs	https://doi.org/10.3762/bjoc.9.99
Publication status	Published - May 3 2013
Externally published	Yes

Keywords

Agelastatin
Aminohalogenation
Free radical
Iron(II)
Natural product synthesis

ASJC Scopus subject areas

Organic Chemistry

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10.3762/bjoc.9.99

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title = "Formal synthesis of (-)-agelastatin A: An iron(II)-mediated cyclization strategy",

abstract = "An iron(II)-mediated aminohalogenation of a cyclopentenyl N-tosyloxycarbamate provided new access to the key intermediate for the synthesis of (-)-agelastatin A (AA, 1), a potent antiproliferative alkaloid. The present synthetic endeavour offered an insight into the mechanism underlying the iron(II)-mediated aminohalogenation of N-tosyloxycarbamate, in which the radical properties of the N-iron intermediates in the redox states were operative.",

keywords = "Agelastatin, Aminohalogenation, Free radical, Iron(II), Natural product synthesis",

author = "Daisuke Shigeoka and Takuma Kamon and Takehiko Yoshimitsu",

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doi = "10.3762/bjoc.9.99",

language = "English",

volume = "9",

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T1 - Formal synthesis of (-)-agelastatin A

T2 - An iron(II)-mediated cyclization strategy

AU - Shigeoka, Daisuke

AU - Kamon, Takuma

AU - Yoshimitsu, Takehiko

PY - 2013/5/3

Y1 - 2013/5/3

N2 - An iron(II)-mediated aminohalogenation of a cyclopentenyl N-tosyloxycarbamate provided new access to the key intermediate for the synthesis of (-)-agelastatin A (AA, 1), a potent antiproliferative alkaloid. The present synthetic endeavour offered an insight into the mechanism underlying the iron(II)-mediated aminohalogenation of N-tosyloxycarbamate, in which the radical properties of the N-iron intermediates in the redox states were operative.

AB - An iron(II)-mediated aminohalogenation of a cyclopentenyl N-tosyloxycarbamate provided new access to the key intermediate for the synthesis of (-)-agelastatin A (AA, 1), a potent antiproliferative alkaloid. The present synthetic endeavour offered an insight into the mechanism underlying the iron(II)-mediated aminohalogenation of N-tosyloxycarbamate, in which the radical properties of the N-iron intermediates in the redox states were operative.

KW - Agelastatin

KW - Aminohalogenation

KW - Free radical

KW - Iron(II)

KW - Natural product synthesis

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DO - 10.3762/bjoc.9.99

M3 - Article

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AN - SCOPUS:84877304709

SN - 1860-5397

VL - 9

SP - 860

EP - 865

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

Formal synthesis of (-)-agelastatin A: An iron(II)-mediated cyclization strategy

Abstract

Keywords

ASJC Scopus subject areas

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