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Chirons 1 and 2, both from mannitol, were used to prepare enantiomerically pure cis and trans stereoisomers of 2,3-methanoglutamine (cyclo-Gln) in a protected form suitable for solid phase peptide synthesis.
All four stereoisomers of the 2,3-methanoamino acids BOC-E-cyclo-Leu and BOC-Z-cyclo-Leu were prepared from the optically active diol 4 (and its enantiomer) derived from valine. The challenges associated with introducing protected amine functionalities cis to the side chain were overcome by using the vinylogous malonate synthon, dimethyl gluconate.
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