Total synthesis of PGF2α and 6,15-diketo-PGF1α and formal synthesis of 6-keto-PGF1α via three-component coupling
| Autor: | Taehyeong Kim, Do Hyun Ryu, Sejin Kim, Sung Il Lee, Su Yong Shim |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
Coupling
010405 organic chemistry Component (thermodynamics) Stereochemistry Organic Chemistry Total synthesis 010402 general chemistry Metathesis 01 natural sciences Biochemistry Coupling reaction 0104 chemical sciences chemistry.chemical_compound chemistry Drug Discovery Wittig reaction Side chain Cyclopentane |
| Zdroj: | Tetrahedron. 75:130593 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2019.130593 |
| Popis: | The asymmetric total synthesis of PGF2α and 6,15-diketo-PGF1α and formal synthesis of 6-keto-PGF1α from a common key intermediate are described. The key intermediate, which has a chiral cyclopentane backbone possessing suitable functional groups with required stereochemistry for both side chains, was prepared from (R)-4-silyloxy-2-cyclopentenone through a three-component coupling reaction. The Wittig reaction, Nozaki-Hiyama-Kishi (NHK) coupling and cross metathesis completed the synthesis of PGF2α, 6,15-diketo-PGF1α and 6-keto-PGF1α. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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