Total Synthesis of the Chlorinated Pentacyclic Indole Alkaloid (+)-Ambiguine G
| Autor: | Viresh H. Rawal, Lingbowei Hu |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
Natural product Ketone Halogenation Indole alkaloid Stereochemistry Communication Molecular Conformation Total synthesis Stereoisomerism General Chemistry Biochemistry Chemical synthesis Catalysis Cycloaddition Indole Alkaloids chemistry.chemical_compound Colloid and Surface Chemistry chemistry Yield (chemistry) Enone |
| Zdroj: | Journal of the American Chemical Society |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/jacs.1c05762 |
| Popis: | Reported herein is the total synthesis of (+)-ambiguine G, the first member of the chlorinated pentacyclic ambiguines to yield to chemical synthesis. The synthesis is accomplished through a convergent strategy that proceeds in 10 steps from (S)-carvone oxide. Pivotal to the concise route is the successful realization of a [4+3] cycloaddition that conjoins two easily synthesized components of the carbon framework of the natural product. Also featured in the synthesis is the efficient, diastereoselective construction of a key vinylated chloro ketone and the unprecedented, one-pot reduction–elimination–oxidation sequence that transforms an enone to an advanced hydroxylated-diene intermediate. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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