Flexible total synthesis of biphenomycin B.

@article{Waldmann2008FlexibleTS,
  title={Flexible total synthesis of biphenomycin B.},
  author={Herbert Waldmann and Yu-Peng He and Hao Tan and Lars Arve and Hans‐Dieter Arndt},
  journal={Chemical communications},
  year={2008},
  volume={43},
  pages={
          5562-4
        }
}
A total synthesis of the biaryl antibiotic biphenomycin B is reported which makes use of three independent building blocks (key steps were a clean Suzuki-Miyaura coupling of a free acid iodide, a novel 4-hydroxyornithine synthesis, and a high-yielding macrolactamization); a practical deprotection protocol allowed isolation of the target compound with excellent recovery and purity. 
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25 Citations

25 Citations

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Citation Type

Scalable Synthesis of the Desoxy-biphenomycin B Core
TLDR
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.
Biphenomycin B and derivatives: total synthesis and translation inhibition.
A full account on the synthesis of the antibiotic natural product biphenomycin B and several derivatives is reported, which employs a Suzuki coupling reaction of a free carboxylic acid and…
Diversity-oriented synthesis and cytotoxic activity evaluation of biaryl-containing macrocycles.
Synthesis of biaryl-containing macrocycles has been carried out through a four-step approach comprising two Ugi four component reactions and a Suzuki-Miyaura macrocyclization. This protocol allowed…
Synthesis of Fmoc-Protected Arylphenylalanines (Bip Derivatives) via Nonaqueous Suzuki-Miyaura Cross-Coupling Reactions.
A one-step synthesis of Fmoc-protected aryl/heteroaryl-substituted phenylalanines (Bip derivatives) using the nonaqueous palladium-catalyzed Suzuki-Miyaura cross-coupling (SMC) reaction of…
Intramolecular Suzuki-Miyaura reaction for the total synthesis of signal peptidase inhibitors, arylomycins A(2) and B(2).
TLDR
Key features of the approach includeformation of 14-membered meta, meta-cyclophane by an intramolecular Suzuki-Miyaura reaction and segment coupling of a fully elaborated peptide side chain to the macrocycle, which makes the synthesis highly convergent.
Solid-Phase Synthesis of Biaryl Cyclic Peptides Containing a 3-Aryltyrosine
A concise and efficient solid-phase synthesis of biaryl cyclic peptides containing a Phe–Tyr or a Tyr–Tyr linkage has been accomplished. The key steps include a Miyaura borylation of a resin-bound…
Solution-phase total synthesis of teixobactin.
TLDR
The first solution-phase total synthesis of the cyclic depsipeptide teixobactin is described, and the protective groups for the peptide coupling reactions and conditions for the assembly of the fragments were also optimised.
Solid-phase synthesis of biaryl cyclic peptides by borylation and microwave-assisted intramolecular Suzuki–Miyaura reaction
The Suzuki–Miyaura Cross-Coupling as a Versatile Tool for Peptide Diversification and Cyclization
TLDR
The Suzuki–Miyaura reaction is a tool to induce the desired cyclization of peptides and diverse amino acid and peptide-based applications explored by means of this extremely versatile cross-coupling reaction are discussed.
Strained cyclophane natural products: macrocyclization at its limits.
TLDR
The challenges synthetic chemists are facing during the synthesis of this small, but structurally and biologically fascinating class of natural products are described, concentrating on the representatives exhibiting configurational stability.
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[reaction: see text] A concise and efficient total synthesis of biphenomycin B has been accomplished featuring a key microwave-assisted intramolecular Suzuki-Miyaura reaction for formation of the…
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