Total Synthesis of Peloruside A through Kinetic Lactonization and Relay Ring-Closing Metathesis Cyclization Reactions
Autor: | Troy D. Ryba, Thomas R. Hoye, Junha Jeon, Manomi A. Tennakoon, Yini Wang, Lucas C. Kopel |
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Rok vydání: | 2010 |
Předmět: |
chemistry.chemical_classification
Biological Products Valerolactone Ketone Chemistry Stereochemistry Total synthesis Stereoisomerism General Chemistry Bridged Bicyclo Compounds Heterocyclic Metathesis Article Catalysis Kinetics Lactones Ring-closing metathesis Aldol reaction Cyclization Peloruside A Dicarboxylic Acids Lactone |
Zdroj: | Angewandte Chemie International Edition. 49:6151-6155 |
ISSN: | 1433-7851 |
DOI: | 10.1002/anie.201002293 |
Popis: | A convergent total synthesis of peloruside A (1) is described. The key strategic features are a diastereoselective lactonization to generate a C5-C9 valerolactone from the C2-symmetric ketone 4, which comprises C1–C9 of 1, and a relay ring closing metathesis (RRCM) reaction to produce a dehydrovalerolactone 20, which embodies C13–C19. A new isomer of 1, the valerolactone iso-peloruside A (iso-1), was identified. |
Databáze: | OpenAIRE |
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