A Synthetic Approach to Ervatamine-Silicine Alkaloids. Enantioselective Total Synthesis of (−)-16-Episilicine

A Synthetic Approach to Ervatamine-Silicine Alkaloids. Enantioselective Total Synthesis of (−)-16-Episilicine

Starting from an appropriate unsaturated phenylglycinol-derived oxazolopiperidone lactam, the synthesis of (−)-16-episilicine is reported, the key steps being a stereoselective conjugate addition, a stereoselective alkylation, and a ring-closing metathesis reaction. This represents the first enantio...

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Veröffentlicht in:Journal of organic chemistry 2010-01, Vol.75 (1), p.178-189
Hauptverfasser: Amat, Mercedes, Llor, Núria, Checa, Begoña, Molins, Elies, Bosch, Joan
Format: Artikel
Sprache:eng
Schlagworte:
Alkaloids - chemical synthesis
Alkaloids - chemistry
Catalysis
Chemistry
Contraindications
Crystallography, X-Ray
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Lactams - chemistry
Molecular Structure
Organic chemistry
Preparations and properties
Secologanin Tryptamine Alkaloids
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Zusammenfassung:Starting from an appropriate unsaturated phenylglycinol-derived oxazolopiperidone lactam, the synthesis of (−)-16-episilicine is reported, the key steps being a stereoselective conjugate addition, a stereoselective alkylation, and a ring-closing metathesis reaction. This represents the first enantioselective total synthesis of an alkaloid of the silicine group.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo902346j