Biomimetic Synthesis of Azole‐ and Aryl‐Peptide Alkaloids

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.

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Biomimetic Synthesis of Azole‐ and Aryl‐Peptide Alkaloids

Cited by 2 publications

References 177 publications

ChemInform Abstract: Biomimetic Synthesis of Azole‐ and Aryl‐Peptide Alkaloids

ChemInform Abstract: Biomimetic Synthesis of Azole‐ and Aryl‐Peptide Alkaloids

Biomimetic Synthesis of Urukthapelstatin A by Aza‐Wittig Ring Contraction

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