Total Synthesis of (+)-Isoschizandrin Utilizing a Samarium(II) Iodide-Promoted 8-Endo Ketyl−Olefin Cyclization
| Autor: | Kelly M. George, Lauren G. Monovich, Gary A. Molander |
|---|---|
| Rok vydání: | 2003 |
| Předmět: |
Boron Compounds
Stereochemistry Samarium(II) iodide chemistry.chemical_element Alkenes Medicinal chemistry Lignans Kinetic resolution Cyclooctanes Lactones chemistry.chemical_compound Ketyl Polycyclic Compounds Schisandra chemistry.chemical_classification Aza Compounds Samarium Atropisomer Olefin fiber Molecular Structure Organic Chemistry Total synthesis Stereoisomerism Iodides Ketones Models Chemical chemistry Cyclization Lactone |
| Zdroj: | The Journal of Organic Chemistry. 68:9533-9540 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | The 13-step synthesis of (+)-isoschizandrin reported herein features a samarium(II) iodide-promoted 8-endo ketyl-olefin coupling to assemble the eight-membered ring present in the target concomitantly with the required functionality and stereochemistry. In constructing (+)-isoschizandrin as a single atropisomer, the synthesis utilizes a kinetic resolution of a seven-membered lactone using a CBS-oxazaborolidine. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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