Diastereoselective Construction of Quaternary Carbons Directed via Macrocyclic Ring Conformation: Formal Synthesis of (−)-Mesembrine
| Autor: | Christiane M. Grisé, Irina Denissova, Louis Barriault, Steve Arns, Marie-Eve Lebrun |
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| Rok vydání: | 2007 |
| Předmět: |
Macrocyclic Compounds
Magnetic Resonance Spectroscopy Alkylation Chemistry Stereochemistry Organic Chemistry Molecular Conformation Total synthesis Stereoisomerism Sequence (biology) Ring (chemistry) Chemical synthesis Carbon Indole Alkaloids Formal synthesis chemistry.chemical_compound Models Chemical Mesembrine Cope rearrangement |
| Zdroj: | The Journal of Organic Chemistry. 72:9314-9322 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo701833v |
| Popis: | In this article, we report a highly diastereoselective new method for the generation of quaternary carbon centers through an anionic oxy-Cope/alkylation sequence where the diastereoselectivity is induced by the conformation of a macrocyclic tetrasubstituted enolate. The use of our methodology culminated in the formal total synthesis of (-)-mesembrine (34) in 11 steps from known starting materials. |
| Databáze: | OpenAIRE |
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