Total synthesis and absolute configuration of the natural amino acid tetrahydrolathyrine.
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.
Benohoud
Meryem
M
Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, UPR 2301, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
Leman
Loic
L
Cardoso
Silvia H
SH
Retailleau
Pascal
P
Dauban
Philippe
P
Thierry
Josiane
J
Dodd
Robert H
RH
D000599:Amino Acids, Diamino / Q000138:chemical synthesis* / Q000737:chemistry; D001685:Biological Factors / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D000599:Amino Acids, Diamino; D001685:Biological Factors; C015317:lathyrine