ChemInform Abstract: An Approach to 2,3-Methanoamino Acids with Extended Side Chains: Syntheses of trans-BOC-cyclo-Lys(CBZ)-OH, trans-BOC-cyclo-Glu-OEt, and trans-BOC-cyclo-Arg(CBZ)-OH.

✍ Scribed by D. LIM; K. BURGESS

• Book ID: 101864478
• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 39 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199819205

✦ Synopsis

An Approach to 2,3-Methanoamino Acids with Extended Side Chains: Syntheses of trans-BOC-cyclo-Lys(CBZ)-OH, trans-BOC-cyclo-Glu-OEt, and trans-BOC-cyclo-Arg(CBZ)-OH.

-A preparation of the cyclopropane chiron (IV) from L-malic acid (I) and reaction sequences are reported, which demonstrate that (IV) is well-suited to syntheses of the hitherto less accessible cyclopropyl analogues of amino acids. This starting material is specifically useful for the title compounds as proven by the preparation of (IX), (X), and (XII). -(LIM, D.;