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

doi:10.3987/COM-06-10683

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

College of Science

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

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 language	English
Pages (from-to)	915-932
Number of pages	18
Journal	Heterocycles
Volume	68
Issue number	5
DOIs	https://doi.org/10.3987/COM-06-10683
Publication status	Published - 2006 May 1

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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

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.",

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AU - Lee, Hong Woo

AU - Ahn, Joong Bok

AU - Lee, Jung Hwa

AU - Kang, Sung Kwon

AU - Ahn, Soon Kil

AU - Ha, Deok Chan

PY - 2006/5/1

Y1 - 2006/5/1

N2 - 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.

AB - 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.

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SN - 0385-5414

IS - 5

ER -

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

Abstract

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