Total Synthesis of the Epoxy Isoprostane Phospholipids PEIPC and PECPC
| Autor: | Judith A. Berliner, Daniela Angst, Lukasz Koroniak, Rongsong Li, Dawei Yue, and Andrew D. Watson, Michael E. Jung |
|---|---|
| Rok vydání: | 2005 |
| Předmět: |
Sharpless epoxidation
chemistry.chemical_classification Isoprostane Ketone Molecular Structure Silylation Stereochemistry Organic Chemistry Total synthesis Isoprostanes Biochemistry chemistry.chemical_compound Enzyme chemistry Phosphatidylcholines Epoxy Compounds Molecule Physical and Theoretical Chemistry Derivative (chemistry) |
| Zdroj: | Organic Letters. 7:3933-3935 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | A total synthesis of the naturally occurring hydroxy ketone PEIPC 1, a compound that plays a role in endothelial activation in atherosclerosis, has been completed via a triply convergent preparation of a protected EI derivative 13 from 3,5-diacetoxycyclopentene 7, pentane-1,5-diol, and vinyllithium, using Sharpless epoxidation and enzymatic resolution as key steps. Final coupling with lyso-PC 16 and silyl group deprotection gave PECPC 2 and PEIPC 1, which showed the same activity as natural PECPC and PEIPC. [reaction: see text] |
| Databáze: | OpenAIRE |
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