Asymmetric synthesis of 7-aza-phomopsolide E and its C-4 epimer
| Autor: | George A. O'Doherty, Miaosheng Li, Alhanouf Z Aljahdali, Seth A. Freedman |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Natural product Ketone 010405 organic chemistry Stereochemistry Organic Chemistry Enantioselective synthesis Noyori asymmetric hydrogenation Alcohol 010402 general chemistry 01 natural sciences Biochemistry Chloride 0104 chemical sciences chemistry.chemical_compound chemistry Drug Discovery medicine Side chain Epimer medicine.drug |
| Zdroj: | Tetrahedron. 74:7121-7126 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2018.10.036 |
| Popis: | A flexible, enantioselective route to highly functionalized α,β-unsaturated δ-lactones has been applied to the synthesis of 7-aza-phomopsolide E and its C-4 epimer. This approach relies on the application of the Noyori asymmetric hydrogenation of furyl ketone to produce the secondary furyl alcohol in high enantioexcess, which can be stereoselectively transformed into α,β-unsaturated-δ-lactones by a short, highly diastereoselective oxidation and reduction sequence. DCC and acid chloride couplings were used to introduce the side chains of the two natural product analogues. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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