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Synfacts 2006(2): 0175-0175  
DOI: 10.1055/s-2005-921773
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

A Traceless Solid-Phase Approach to Functionalized Tetramic Acids

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Tomohiko Beppu
K. C. Prousis, A. D. Detsi, O. Igglessi-Markopoulou*
National Technical University of Athens, Greece
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Publication History

Publication Date:
23 January 2006 (online)

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Significance

A traceless synthesis of functionalized tetramic acids was reported. Reaction of the carbamate resin 1 with amino acids 2 gave the carbamate-protected amino acids 3. C-Acylation of activated methylene compounds 4 with 3 gave the corresponding carbamate resin 5. Cleavage and subsequent cyclization were achieved by treatment of resin 5 with TFA-CH2Cl2 to give tetramic acid derivatives in good yields (74-82%) and enantioselectivities (80-84%).