Synthesis of 3-hydroxyindolin-2-one alkaloids, (±)-donaxaridine and (±)-convolutamydines A and E, through enolization–Claisen rearrangement of 2-allyloxyindolin-3-ones

Claisen rearrangement triggered by enolization of 2-allyloxyindolin-3-ones with DBU was performed in order to prepare 3-allyl-3-hydroxyindolin-2-ones. Total synthesis of 3-hydroxyindolin-2-one alkaloids, (±)-donaxaridine, as well as (±)-convolutamydines A and E, was achieved by transformation of the...

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Bibliographic Details
Published in:Tetrahedron 2004-04, Vol.60 (15), p.3493-3503
Main Authors: Kawasaki, Tomomi, Nagaoka, Miyuki, Satoh, Tomoko, Okamoto, Ayako, Ukon, Rie, Ogawa, Atsuyo
Format: Article
Language:English
Subjects:
Allylalcohol
DBU
Molybdenum peroxide
Osmium tetraoxide
Wacker oxidation
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Summary:Claisen rearrangement triggered by enolization of 2-allyloxyindolin-3-ones with DBU was performed in order to prepare 3-allyl-3-hydroxyindolin-2-ones. Total synthesis of 3-hydroxyindolin-2-one alkaloids, (±)-donaxaridine, as well as (±)-convolutamydines A and E, was achieved by transformation of the allyl moiety of 3-allyl-3-hydroxyindolin-2-ones. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.02.031