Unified synthesis of caged Garcinia natural products based on a site-selective Claisen/Diels–Alder/Claisen rearrangement
| Autor: | Emmanuel A. Theodorakis, Eric J. Tisdale, Irina Slobodov |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2004 |
| Předmět: |
chemistry.chemical_classification
Steric effects Bridged-Ring Compounds Biological Products Multidisciplinary biology Molecular Structure Stereochemistry Xanthones Chemistry Organic biology.organism_classification Forbesione Claisen rearrangement chemistry.chemical_compound A-site chemistry Xanthenes Heterocyclic Compounds Xanthone Diels alder Indicators and Reagents Bridged compounds Garcinia Natural Product Synthesis Special Feature |
| Popis: | A unified synthetic strategy toward caged Garcinia natural products has been designed and implemented. Central to the strategy is a tandem Claisen/Diels–Alder/Claisen rearrangement of a suitably substituted xanthone precursor to form forbesione (1a). Serving as a template, forbesione is then used to deliver representative members of this family, including desoxygaudichaudione A (4), desoxymorellin (5), and gambogin (10). Studies on the timing of this reaction cascade suggest that the C-ring Claisen/Diels–Alder rearrangement proceeds initially and is followed by the A-ring Claisen reaction. The electronic and steric effects that govern the outcome of this cascade are presented. |
| Databáze: | OpenAIRE |
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