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

Fingerprint

Selenium Oxides
Esters
Derivatives
Molecules
fumagillol

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Selective N-demethylation of tertiary aminofumagillols with selenium dioxide via a non-classical Polonovski type reaction. / Lee, Hong Woo; Ahn, Joong Bok; Lee, Jung Hwa; Kang, Sung Kwon; Ahn, Soon Kil; Ha, Deok-Chan.

In: Heterocycles, Vol. 68, No. 5, 01.05.2006, p. 915-932.

Research output: Contribution to journalArticle

Lee, Hong Woo ; Ahn, Joong Bok ; Lee, Jung Hwa ; Kang, Sung Kwon ; Ahn, Soon Kil ; Ha, Deok-Chan. / Selective N-demethylation of tertiary aminofumagillols with selenium dioxide via a non-classical Polonovski type reaction. In: Heterocycles. 2006 ; Vol. 68, No. 5. pp. 915-932.
@article{2564c48a1d1a4fd98ccd51a9f23955e1,
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.",
author = "Lee, {Hong Woo} and Ahn, {Joong Bok} and Lee, {Jung Hwa} and Kang, {Sung Kwon} and Ahn, {Soon Kil} and Deok-Chan Ha",
year = "2006",
month = "5",
day = "1",
doi = "10.3987/COM-06-10683",
language = "English",
volume = "68",
pages = "915--932",
journal = "Heterocycles",
issn = "0385-5414",
publisher = "Japan Institute of Heterocyclic Chemistry",
number = "5",

}

TY - JOUR

T1 - Selective N-demethylation of tertiary aminofumagillols with selenium dioxide via a non-classical Polonovski type reaction

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.

UR - http://www.scopus.com/inward/record.url?scp=33745756383&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33745756383&partnerID=8YFLogxK

U2 - 10.3987/COM-06-10683

DO - 10.3987/COM-06-10683

M3 - Article

AN - SCOPUS:33745756383

VL - 68

SP - 915

EP - 932

JO - Heterocycles

JF - Heterocycles

SN - 0385-5414

IS - 5

ER -