Atelia herbert-smithii

From the seeds of the legume Atelia herbert smithii Pittier (Papilionidae), which seems to repel insect predators, Bell et al. have isolated the new amino acid 2,4-methanoproline (56) (98). This structure has been established by spectroscopic means and confirmed by X-ray diffraction. 

From Ser via methyl 2-benzamido-3-chloropropionate, an azahexadiene was prepared which was photocyclized and hydrolyzed to the bicyclic amino acid 14 which is found in the Atelia Herbert Smithii plant (88JOC4793). 

Austin, G. N., P. D. Baird, H. Chow, L. E. Fellows, G. W. J. Fleet, R. J. Nash, J. M. Peach, R. J. Pryce, and C. H. Stirton, Isolation from Atelia herbert-smithii Pittier (Sophoreae, Leguminosae) and x-ray structure of ds-l-amino-3-hydroxy-methylcyclobutane-l-carboxylic acid, an achiral non-protein amino acid, Tetrahedron, 43, 1857-1861 (1987). 

Minor component of the Costa Rican legume Atelia Herbert smithii and of other A. and Cyanthiostegia spp. Cryst. (EtOH aq.). Mp 250-260° dec. (synthetic)(210°). B,HCl [109826-20-2]. 

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