339315-18-3Relevant articles and documents
An unexpected formation of a 14-membered cyclodepsipeptide
Iliev, Boyan,Linden, Anthony,Heimgartner, Heinz
, p. 3215 - 3234 (2007/10/03)
The treatment of diluted solutions of the hydroxy diamides 6a and 6b in toluene with HCl gas at 100° gave the dimeric, 14-membered cyclodepsipeptide 10 in up to 72% yield (Scheme 3). The same product was formed from the linear dimer of 6b, the depsipeptid
Synthesis of conformationally restricted cyclic pentadepsipeptides via direct amide cyclization
Koch, Kristian N,Linden, Anthony,Heimgartner, Heinz
, p. 2311 - 2326 (2007/10/03)
The 2,2-disubstituted 2H-azirin-3-amines 6 (3-amino-2H-azirines) were used as building blocks for α,α-disubstituted α-amino acids in the preparation of 16-membered cyclic depsipeptides 14. The linear precursors containing four α,α-disubstituted α-amino acids, the pentapeptides 13, were synthesized starting with β-hydroxy acids 5 via the 'azirine/oxazolone method'. The cyclic depsipeptides 14 were formed via 'direct amide cyclization' and the influence of several factors on this cyclization was investigated in the following way: (a) using the same composition of α,α-disubstituted α-amino acids, but changing their respective positions in the peptide chain; (b) using different C-terminal α,α-disubstituted α-amino acids in the peptide chain; (c) using different β-hydroxy acids; and (d) using different diastereoisomers of the peptides.