Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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mCPBA Oxidation of Acetyllycoctonine and Its New Products
Xiang-Li Shen, Feng-Peng Wang
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Keywords: C19-diterpenoid alkaloid, acetyllycoctonine, oxidation involving nitrogen atom, N-oxidation
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2005 Volume 53 Issue 3 Pages 267-270

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Abstract

Treatment of a lycoctonine-type alkaloid acetyllycoctonine (4) with mCPBA at room temperature led to acetyllycoctonine N-oxide (5) as the major product together with other interesting compounds 6—12 as the minor products, which were derived from oxidation involving the nitrogen atom and Cope elimination as well as Polonovski-like fragmentation. All of those new compounds (5—12) were fully characterized.

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© 2005 The Pharmaceutical Society of Japan
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