890085-24-2Relevant academic research and scientific papers
Biomimetic Synthesis of Urukthapelstatin A by Aza-Wittig Ring Contraction
Schwenk, Sebastian,Ronco, Cyril,Oberheide, Ansgar,Arndt, Hans-Dieter
, p. 4795 - 4799 (2016/10/13)
Marine bacteria produce highly cytotoxic polyheterocyclic cyclopeptide natural products by ribosomal peptide biosynthesis. Among them, urukthapelstatin A features a chain of five 2,4′-connected azole rings within a cyclo-octapeptide framework. We report a novel synthesis design that uses only α-amino acids as starting materials that leads to an efficient and stereoselective total synthesis of urukthapelstatin A. Kinetically favored macro-thiolactonization and high-yielding aza-Wittig heterocyclization to contract the macrocycle were crucial for success. These investigations additionally uncovered the unsuspected configurational lability of the embedded enamide substructure in solution.
Total synthesis and biological activity of natural product Urukthapelstatin A
Lin, Chun-Chieh,Tantisantisom, Worawan,McAlpine, Shelli R.
supporting information, p. 3574 - 3577 (2013/08/23)
Herein we report the first total synthesis of the natural product Urkuthaplestatin A (Ustat A) utilizing a convergent synthetic strategy. The characterization and biological activity match those of the previously published natural product. Interestingly,
