Oxidation of indolines to nitrones and new rearrangement in seco-curane type indoline alkaloids

At room temperature 3-chloroperoxybenzoic acid oxidizes the deacetylated strychnobrasiline to the corresponding nitrone. Two unexpected rearrangements are observed when the reaction is performed at 40°C. Graphic

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Bibliographic Details
Published in:Tetrahedron 2002-05, Vol.58 (22), p.4555-4558
Main Authors: Trigalo, François, Martin, Marie-Thérèse, Rasolondratovo, Benoı̂t, Blond, Alain, Youte, Jean Jacques, Rasoanaivo, Philippe, Frappier, François
Format: Article
Language:English
Subjects:
15N NMR
alkaloid
Baeyer–Villiger reaction
Biochemistry
Biochemistry, Molecular Biology
indoline
Life Sciences
nitrone
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Description
Summary:At room temperature 3-chloroperoxybenzoic acid oxidizes the deacetylated strychnobrasiline to the corresponding nitrone. Two unexpected rearrangements are observed when the reaction is performed at 40°C. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)00407-6