Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 28, Pages 4795-4799Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201600994
Keywords
Amino acids; Cyclization; Cyclopeptides; Macrocycles; Stereoselectivity; Total synthesis
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Funding
- Alexander-von-Humboldt Foundation
- Thuringer Ministerium fur Wissenschaft, Wirtschaft und Digitale Gesellschaft (TMWWDG) [43-5572-321-12040-12]
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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 alpha-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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