2009•The Journal of Organic ChemistryRequires access
Total Synthesis and Absolute Configuration of the Natural Amino Acid Tetrahydrolathyrine
Meryem Benohoud, Loı̈c Leman, Sílvia Helena Cardoso, Pascal Retailleau, Philippe Dauban, Josiane Thierry, Robert H. Dodd
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Abstract
The natural product tetrahydrolathyrine has been synthesized through an iminoiodane-mediated aziridination of a (2S)-allylglycinol derivative, which provided a 2:3 mixture of diastereoisomers. One of these diastereoisomers was converted to the natural product and the other to its C-4 epimer. The C-4 configuration was established from NOESY NMR analysis and X-ray structure of compounds derived from the non-natural diastereoisomer. Thus, tetrahydrolathyrine was shown to have the (2S,4R) absolute configuration.