170111-76-9Relevant academic research and scientific papers
Total syntheses of linear polythiazole/oxazole plantazolicin A and its biosynthetic precursor plantazolicin B
Wilson, Zoe E.,Fenner, Sabine,Ley, Steven V.
, p. 1284 - 1288 (2015)
Plantazolicin A, a linear decacyclic natural product, exhibits desirable selective activity against the causative agent of anthrax toxicity. The total synthesis of plantazolicin A and its biosynthetic precursor plantazolicin B was successfully achieved by an efficient, unified, and highly convergent route featuring dicyclizations to form 2,4-concatenated oxazoles and the mild synthesis of thiazoles from natural amino acids. This report represents the first synthesis of plantazolicin B and includes the first complete characterization data for both natural products.
The Total Synthesis of the Bioactive Natural Product Plantazolicin A and Its Biosynthetic Precursor Plantazolicin B
Fenner, Sabine,Wilson, Zoe E.,Ley, Steven V.
supporting information, p. 15902 - 15912 (2016/10/24)
Herein, we describe our full investigations into the synthesis of the peptide-derived natural product plantazolicin A, a compound that demonstrates promising selective activity against the causative agent of anthrax toxicity, and its biosynthetic precurso
High-Temperature Boc Deprotection in Flow and Its Application in Multistep Reaction Sequences
Bogdan, Andrew R.,Charaschanya, Manwika,Dombrowski, Amanda W.,Wang, Ying,Djuric, Stevan W.
supporting information, p. 1732 - 1735 (2016/05/19)
A simplified Boc deprotection using a high-temperature flow reactor is described. The system afforded the qualitative yield of a wide variety of deprotected substrates within minutes using acetonitrile as the solvent and without the use of acidic conditions or additional workups. Highly efficient, multistep reaction sequences in flow are also demonstrated wherein no extraction or isolation was required between steps.
Total Synthesis of the Posttranslationally Modified Polyazole Peptide Antibiotic Plantazolicin A
Wada, Hiroki,Williams, Huw E. L.,Moody, Christopher J.
supporting information, p. 15147 - 15151 (2016/01/25)
The power of rhodium-carbene methodology in chemistry is demonstrated by the synthesis of a structurally complex polyazole antibiotic. Plantazolicin A, a novel soil-bacterium metabolite, comprises a linear array of 10 five-membered rings in two pentacycli
Total synthesis of the ribosomally synthesized linear azole-containing peptide plantazolicin a from bacillus amyloliquefaciens
Banala, Srinivas,Ensle, Paul,Süssmuth, Roderich D.
, p. 9518 - 9523 (2013/09/23)
A cyclodehydration reaction has been used to synthesize the linear azole-containing peptide plantazolicin A. The target compound was synthesized from two heterocyclic fragments derived from dipeptide building blocks. The acid-labile oxazolines and thiazoles necessitate the use of a Teoc/TMSE-based protection-group strategy, which allows structure modification of plantazolicin. Copyright
