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 | |
| Publication status | Published - 2006 May 1 |
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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 journal › Article
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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
VL - 68
SP - 915
EP - 932
JO - Heterocycles
JF - Heterocycles
SN - 0385-5414
IS - 5
ER -