108890-90-0Relevant articles and documents
Application of Negishi cross-coupling to the synthesis of the cyclic tripeptides OF4949-III and K-13
Nolasco, Luca,Gonzalez, Manuel Perez,Caggiano, Lorenzo,Jackson, Richard F. W.
experimental part, p. 8280 - 8289 (2010/02/17)
(Chemical Equation Presented) Syntheses of the cyclic tripeptides OF4949-III 1 and K-13 2 are reported, in which the key steps are intermolecular and intramolecular Negishi cross-coupling reactions, respectively. In addition, the synthesis of a protected
Mild and nonracemizing conditions for Ullmann-type diaryl ether formation between aryl iodides and tyrosine derivatives
Cai, Qian,He, Gang,Ma, Dawei
, p. 5268 - 5273 (2007/10/03)
CuI/N,N-dimethylglycine-catalyzed coupling reaction of L-tyrosine derivatives and L-phenylalanine-derived iodides in the presence of Cs 2CO3 works at 90 °C to provide the corresponding diaryl ether. Partial racemization occurs when N
Mild Ullmann-type biaryl ether formation reaction by combination of ortho-substituent and ligand effects
Cai, Qian,Zou, Benli,Ma, Dawei
, p. 1276 - 1279 (2007/10/03)
(Chemical Equation Presented) An important position: A strong orthosubstituent effect caused by NHCOR groups in 2-haloacetanilides in combination with the ligand effect greatly promotes an Ullmann-type biaryl formation reaction that takes place at room te
Pd-catalysed C-C macrocyclisation of a simple tripeptide: Efficient total synthesis of K-13
Perez-Gonzalez,Jackson
, p. 2423 - 2424 (2007/10/03)
The cyclic tripeptide K-13 has been prepared in 11 steps from commercially available starting materials (11% overall yield); the key step is the Pd-catalysed macrocyclisation of the zinc reagent prepared by selective insertion of zinc into the aliphatic C
Total synthesis of the cyclic biphenyl ether peptides K-13 and OF494-III via S(N)Ar macrocyclizations of peptidyl ruthenium π-arene complexes
Janetka, James W.,Rich, Daniel H.
, p. 6488 - 6495 (2007/10/03)
Intramolecular nucleophilic aromatic substitution (S(N)Ar) of preformed ruthenium cyclopentadienyl cationic peptidyl π-complexes forms cyclic biphenyl ethers in convenient, high-yielding reactions. The utility of the method was demonstrated by the efficie
Total Synthesis of L,L-Isodityrosine and Isodityrosine-Derived Agents: K-13, OF4949-III, and OF4949-IV
Boger, Dale L.,Yohannes, Daniel
, p. 6000 - 6017 (2007/10/02)
Full details of the development of reaction conditions for implementation of an activated Ullmann condensation reaction that may be conducted without amino acid racemization and that have proven suitable for incorporation of the selectively protected cate
The total synthesis of the isodityrosine-derived cyclic tripeptides OF4949-III and K-13. Determination of the absolute configuration of K-13
Evans,Ellman
, p. 1063 - 1072 (2007/10/02)
The asymmetric syntheses of the two cyclic tripeptides OF4949-III and K-13 have been completed. The absolute stereochemical assignment of the former compound has been confirmed, while the absolute configuration of the latter has been established for the f
