Stereoselective Total Synthesis of (−)-(2S,4R)-3′-Methoxyl Citreochlorol: Preparation and Use of New Proline-Based Auxiliary for Asymmetric Acetate Aldol Reaction
| Autor: | Reyno R S, Goreti Rajendar, Ranganayakulu Sunnapu, Aleena Thomas, Saikumar Naik Banoth, Navyasree Venugopal |
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| Rok vydání: | 2020 |
| Předmět: |
Chiral auxiliary
Geminal 010405 organic chemistry Stereochemistry Imidazolidinone organic chemicals Organic Chemistry Total synthesis 010402 general chemistry 01 natural sciences 0104 chemical sciences chemistry.chemical_compound chemistry Aldol reaction Amide polycyclic compounds Stereoselectivity Chirality (chemistry) |
| Zdroj: | The Journal of Organic Chemistry. 85:4103-4113 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | The first stereoselective total synthesis of (-)-(2S,4R)-3'-methoxy citreochlorol and (-)-(2S,4S)-3'-methoxy citreochlorol is demonstrated. A proline-based imidazolidinone was synthesized and used as chiral auxiliary for asymmetric acetate aldol reaction to generate initial chirality in the targeted molecule. Geminal dichloromethane functionality was introduced by the addition of in situ generated dichloromethyllithium to Weinreb's amide functional group. |
| Databáze: | OpenAIRE |
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