121124-96-7Relevant academic research and scientific papers
Desymmetrization of Diarylmethylamido Bis(phenols) through Peptide-Catalyzed Bromination: Enantiodivergence as a Consequence of a 2 amu Alteration at an Achiral Residue within the Catalyst
Hurtley, Anna E.,Stone, Elizabeth A.,Metrano, Anthony J.,Miller, Scott J.
supporting information, p. 11326 - 11336 (2017/11/10)
Diarylmethylamido bis(phenols) have been subjected to peptide-catalyzed, enantioselective bromination reactions. Desymmetrization of compounds in this class has been achieved such that enantioenriched products may be isolated with up to 97:3 er. Mechanist
Scalable synthesis of the desoxy-biphenomycin B core
Berwe, Mathias,Joentgen, Winfried,Krueger, Jochen,Cancho-Grande, Yolanda,Lampe, Thomas,Michels, Martin,Paulsen, Holger,Raddatz, Siegfried,Weigand, Stefan
, p. 1348 - 1357 (2012/01/12)
We describe the evolution of a kilogram-scale synthesis of the protected cyclic tripeptide desoxy-biphenomycin B, based on an early discovery route. The retrosynthetic concept included a macrolactamization strategy to build the core ring system of biphenomycin B in combination with a double catalytic asymmetric hydrogenation protocol for the construction of the ansa-tripeptide precursor. Eventually, the kilogram process comprised a 16-step sequence with an overall yield for the longest linear sequence of 19.5%.
Total synthesis of the biphenomycins; III. Synthesis of biphenomycin B
Schmidt,Meyer,Leitenberger,Griesser,Lieberknecht
, p. 1025 - 1030 (2007/10/02)
The total synthesis of the cyclopeptide biphenomycin B (1b), a compound exhibiting a potent antibacterial activity against Gram-positive bacteria, is described. The non-proteinogenic amino acid (S,S)-diisotyrosine (2) was prepared by enantioselective hydrogenation of the corresponding didehydroamino acids. The 15-membered ansa ring was obtained in 85% yield within 5 minutes by ring closure of the appropriate linear pentafluorophenyl ester in the two phase system chloroform-aqueous sodium hydrogen carbonate without dilution.
The Synthesis of Biphenomycin B
Schmidt, Ulrich,Meyer, Regina,Leitenberger, Volker,Lieberknecht, Albrecht,Griesser, Helmut
, p. 275 - 277 (2007/10/02)
Biphenomycin B, a highly potent antibiotic against Gram-negative, β-lactam-resistant bacteria, which was previously isolated from culture filtrates of Streptomyces griseorubiginosus No. 43708, has now been synthesized.
