Enantioselective synthesis of protected nitrocyclohexitols with five stereocenters. Total synthesis of (+)-pancratistatin
| Autor: | Fernando Cagide-Fagín, Ricardo Alonso, Olaia Nieto-García, Hugo Lago-Santomé |
|---|---|
| Rok vydání: | 2012 |
| Předmět: |
Annulation
Natural product Chemistry Stereochemistry Organic Chemistry Enantioselective synthesis Total synthesis Stereoisomerism Chemistry Techniques Synthetic Pancratistatin Isoquinolines Stereocenter Substrate Specificity chemistry.chemical_compound Amaryllidaceae Alkaloids Substrate specificity Inositol |
| Zdroj: | The Journal of organic chemistry. 77(24) |
| ISSN: | 1520-6904 |
| Popis: | 2-Methoxymethylpyrrolidine best performed, among several other proline derivatives, to control the enantioselective [3+3] annulation of β-(hetero)aryl-α-nitro-α,β-enals with commercial 2,2-dimethyl-1,3-dioxan-5-one, a procedure that renders highly oxygenated nitrocyclohexanes endowed with five new stereocenters. Use of this reaction allowed the development of a total synthesis of the antitumoral natural product (+)-pancratistatin; it also converted our previous racemic route to tetrodotoxin into an enantioselective one. |
| Databáze: | OpenAIRE |
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