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Synthesis of cis- and trans-1-amino-3-hydroxymethyl-cyclobutane-1-carboxylic acids

✍ Scribed by George W.J. Fleet; Julio A. Seijas; M.P. Vazquez Tato

Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 239 KB
Volume: 44
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)90351-5

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✦ Synopsis

The stereospecific syntheses of cis-and trans-1-amino-3hydroxymethyl-cyclobutane-1-carboxylz acids from 3-oxabicyclo[3.l.llheptan-2-one-1-carboxylic acid are described. (Recebed in UK 6 Jamrary 1988) The three achiral cyclobutane amino acids, cia-1-amino-3-hydroxymethyl-cyclobutane--1-carhoxylic acid (l),' 2,4-methancqlutamic acid (3) and 2,4-methanoproline (4)' were first isolated from seeds of Atelia herbert-smith11 Pittier (Legumlnosae)j3 the three free cyclobutane amino acids have also been found in the seeds and leaves of four other Atelia species and of both species of the closely related genus Cyathostegia. No synthesis of 2,4-methancglutamic acid (3) has been described; two

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