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An approach towards azafuranomycin analogs by gold-catalyzed cycloisomerization of allenes: synthesis of (αS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine
The synthesis of (αS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine (22, normethylazafuranomycin) by the gold-catalyzed cycloisomerization of α-aminoallene 17 is described. The target molecule was synthesized in 13 linear steps from Cbz-protected Garner aldehyde (R)-2 in an overall yield of 2.4%. The appro...
| Autores principales: | , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
Beilstein-Institut
2013
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3817573/ https://www.ncbi.nlm.nih.gov/pubmed/24204404 http://dx.doi.org/10.3762/bjoc.9.229 |
| Sumario: | The synthesis of (αS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine (22, normethylazafuranomycin) by the gold-catalyzed cycloisomerization of α-aminoallene 17 is described. The target molecule was synthesized in 13 linear steps from Cbz-protected Garner aldehyde (R)-2 in an overall yield of 2.4%. The approach was first examined in model studies, which afforded the alkylated azafuranomycin derivative 13a in 2.9% yield over 12 steps. |
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