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

Daisuke Shigeoka, Takuma Kamon, Takehiko Yoshimitsu

Research output: Contribution to journalArticle

15 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 languageEnglish
Pages (from-to)860-865
Number of pages6
JournalBeilstein Journal of Organic Chemistry
Volume9
DOIs
Publication statusPublished - May 3 2013
Externally publishedYes

Fingerprint

Cyclization
Iron
Alkaloids
agelastatin A

Keywords

  • Agelastatin
  • Aminohalogenation
  • Free radical
  • Iron(II)
  • Natural product synthesis

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Formal synthesis of (-)-agelastatin A : An iron(II)-mediated cyclization strategy. / Shigeoka, Daisuke; Kamon, Takuma; Yoshimitsu, Takehiko.

In: Beilstein Journal of Organic Chemistry, Vol. 9, 03.05.2013, p. 860-865.

Research output: Contribution to journalArticle

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