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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.

SUBMITTER: Shigeoka D

PROVIDER: S-EPMC3678661 | biostudies-other | 2013

REPOSITORIES: biostudies-other

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

Shigeoka Daisuke D Kamon Takuma T Yoshimitsu Takehiko T

Beilstein journal of organic chemistry 20130503

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. ...[more]

PMID: 23766801

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