Diastereo- and Enantiocontrolled Synthesis of (-)-Allosedamine via Cycloaddition of a Chiral Nitrone
| Autor: | Jörg Deerberg, Wolfgang Oppolzer, Osamu Tamura |
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| Jazyk: | angličtina |
| Rok vydání: | 1994 |
| Předmět: |
chemistry.chemical_classification
Chemistry Stereochemistry Organic Chemistry Enantioselective synthesis Biochemistry Aldehyde Catalysis Cycloaddition Nitrone Inorganic Chemistry chemistry.chemical_compound Hydroxylamine Drug Discovery 1 3-Dipolar cycloaddition ddc:540 Piperidine Physical and Theoretical Chemistry Amination |
| Zdroj: | Helvetica Chimica Acta, Vol. 77, No 2 (1994) pp. 554-560 |
| ISSN: | 0018-019X |
| Popis: | The piperidine alkaloid (–)-allosedamine (1) has been synthesized, in 21% overall yield, in nine steps starting from the formyl-ester 4. The synthesis features the reaction cascade 7 → 3 → 2, involving asymmetric electrophilic enolate hydroxyamination, hydroxylamine/aldehyde condensation, and nitrone/styrene cycloaddition, as well as the reductive N/O cleavage-decyanation 12 → 1. |
| Databáze: | OpenAIRE |
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