Formal Synthesis of (+)-Lasubine II and (−)-Subcosine II via Organocatalytic Michael Addition of a Ketone to an α-Nitrostyrene
| Autor: | Sunil V. Pansare, N V G Moorthy, Rajendar Dyapa |
|---|---|
| Rok vydání: | 2015 |
| Předmět: |
chemistry.chemical_classification
Quinolizidines Quinolizidine Ketone Molecular Structure Stereochemistry Organic Chemistry Stereoisomerism Ketones Nitro Compounds Biochemistry Styrenes 3. Good health Stereocenter chemistry.chemical_compound Alkaloids Piperidines Lasubine II chemistry Michael reaction Physical and Theoretical Chemistry Enantiomer Quinolizines |
| Zdroj: | Organic Letters. 17:5312-5315 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.5b02677 |
| Popis: | The first examples of an organocatalytic Michael addition of a ketone to in situ generated α-nitrostyrenes are reported. A suitably functionalized γ-nitroketone obtained from the organocatalyzed Michael addition was converted into (+)-2-epi-lasubine II, the immediate synthetic precursor of (+)-lasubine II and (-)-subcosine II (enantiomers of the natural quinolizidine alkaloids). Two of the three stereocenters in (+)-2-epi-lasubine II are set by the Michael reaction. |
| Databáze: | OpenAIRE |
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