Selective N-demethylation of tertiary aminofumagillols with selenium dioxide via a non-classical Polonovski type reaction

Hong Woo Lee, Joong Bok Ahn, Jung Hwa Lee, Sung Kwon Kang, Soon Kil Ahn, Deok Chan Ha

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The previously unknown selective N-demethylation of tertiary aminofumagillols (5a-e) to the corresponding secondary aminofumagillols (7a-c) is effectively accomplished via a non-classical Polonovski type reaction using selenium dioxide (SeO2). Especially, noteworthy is that two epoxy and the α,β-unsaturated ester functionalities in the fumagillol molecules tolerate in this transformation. Aminofumagillol derivatives are valuable antiangiogenesis inhibitors.

Original languageEnglish
Pages (from-to)915-932
Number of pages18
JournalHeterocycles
Volume68
Issue number5
DOIs
Publication statusPublished - 2006 May 1

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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