Synlett 2003(5): 0627-0630
DOI: 10.1055/s-2003-38355
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

A Highly Efficient Approach to 5-Alkyl-5-hydroxymethyl Substituted 4-O-Benzyl 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)218077247; e-Mail: franz.paintner@cup.uni-muenchen.de;
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Received 20 December 2002
Publikationsdatum:
28. März 2003 (online)

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Abstract

4-O-Benzyl-5-methoxycarbonyl tetramates readily available by 5-methoxycarbonylation of 4-O-benzyl tetramates undergo highly regioselective alkylations with various alkyl halides to give 5-alkyl-4-O-benzyl-5-methoxycarbonyl tetramates in high overall yields. These can be efficiently converted into 5-alkyl-5-hydroxymethyl substituted 4-O-benzyl tetramates and further into the respective tetramic acids.