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Synthesis 2002(7): 0869-0874
DOI: 10.1055/s-2002-28522
PAPER
© Georg Thieme Verlag Stuttgart · New York

A New, General Entry to 3,5-Unsubstituted 4-O-Alkyl Tetramates

Franz F. Paintner*, Marcel Metz, Gerd Bauschke
Department Pharmazie - Zentrum für Pharmaforschung, Ludwig-Maximilians-Universität München, Butenandtstraße 5-13, Haus C, 81377 München, Germany
Fax: +49(89)21807247; e-Mail: ffpai@cup.uni-muenchen.de;
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Publication History

Received 20 March 2002
Publication Date:
14 May 2002 (online)

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Abstract

A variety of 3,5-unsubstituted 4-O-benzyl tetramates 10 was prepared in good overall yield from methyl (E)-3-benzyloxy-4-oxobut-2-enoate 7 by a reductive amination-lactamization sequence. An efficient approach to this building block as well as to various 3-alkoxy analogues is presented.

Key words

tetramic acids - enols - conjugate additions - aminations - lactams

    References and Notes

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