163458-37-5Relevant articles and documents
Synthesis of (+)- and (-)-N-BOC-7-azabicyclo[2.2.1]heptan-2-ones, versatile intermediates for the enantiospecific synthesis of (+)- and (-)-epibatidine and analogues
Hernandez,Marcos,Rapoport
, p. 2683 - 2691 (1995)
(+)- and (-)-Epibatidine, nonopiate antinociceptive alkaloids, have been prepared from (-)- and (+)-N-BOC-7-azabicyclo[2.2.1]heptan-2-one which were produced by resolution of the racemic mixture of the corresponding alcohols obtained in the previous racemic synthesis. In the present work, we report the enantiospecific synthesis of (-)- and (+)-N-BOC-7-azabicyclo[2.2.1]heptan-2-one from L-glutamic acid and levulinic acid. Also, this report describes the selective formation of trans-2,3-disubstituted-7-azabicyclo[2.2.1]heptanes from N-benzyl-5-(1'-methoxycarbonyl-3'-exobutyl)proline via a decarbonylation/iminium ion cyclization process. These functionalized intermediates are of potential value for the enantiospecific synthesis of epibatidine analogues.
Oligomers of β-amino acid bearing non-planar amides form ordered structures
Otani, Yuko,Futaki, Shiroh,Kiwada, Tatsuto,Sugiura, Yukio,Muranaka, Atsuya,Kobayashi, Nagao,Uchiyama, Masanobu,Yamaguchi, Kentaro,Ohwada, Tomohiko
, p. 11635 - 11644 (2007/10/03)
In this report, we explore the feasibility of using bicyclic chiral β-amino acids, (1R,2R,4S)- and (1S,2S,4R)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid (R-Ah2c and S-Ah2c, respectively), to prepare novel peptides with unique properties. Facile cis-trans isomerization of the non-planar amide bonds of these β-amino acids should result in great flexibility of the backbone structure of β-peptides containing them. Indeed, oligomers of these amino acids showed thermostability and characteristic CD absorptions, which were not concentration-dependent, suggesting that the oligomers remained monomeric. The results indicated the formation of self-organized monomeric structures with chain-length-dependent stabilization. Energy calculations suggested that the peptides can take helical structures in which the energy barriers to cis-trans isomerization are greater for the central amide bonds than for the terminal amides.
