Iterative Synthetic Strategy for Azaphenalene Alkaloids. Total Synthesis of (−)-9aepi-Hippocasine
| Autor: | Marta Figueredo, Cristina Oliveras-González, Pau Bayón, Angel Alvarez-Larena, Sílvia Alujas-Burgos |
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| Rok vydání: | 2018 |
| Předmět: |
Models
Molecular 010405 organic chemistry Chemistry Organic Chemistry Molecular Conformation Total synthesis Stereoisomerism Glutarimide Chemistry Techniques Synthetic 010402 general chemistry 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences Tsuji–Trost reaction chemistry.chemical_compound Alkaloids Ring-closing metathesis Nucleophile Stereoselectivity Enantiomer Palladium Derivative (chemistry) |
| Zdroj: | The Journal of Organic Chemistry. 83:5052-5057 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.8b00390 |
| Popis: | A new strategy for the stereoselective synthesis of alkaloids with perhydro-9b-azaphenalene skeleton has been developed. The starting material is the substituted glutarimide derivative 1, readily available in either enantiomeric form through the palladium-catalyzed asymmetric allylic alkylation of glutarimide. The strategy relies on an iterative methodology encompassing two nucleophilic allylations and two ring closing metathesis processes. The approach has been used in the first synthesis of (-)-9a- epi-hippocasine. |
| Databáze: | OpenAIRE |
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