Short synthesis of (±)-hirsutine: Direct addition of dimethyl malonate anion to a 1,4-conjugate iminium salt of appropriate 3-ethylindolo[2,3-a]quinolizidine
| Autor: | Pirjo Hanhinen, Mauri Lounasmaa, Reija Jokela, Jari Miettinen |
|---|---|
| Rok vydání: | 1997 |
| Předmět: |
chemistry.chemical_classification
Quinolizidine 010405 organic chemistry Organic Chemistry Iminium Salt (chemistry) 010402 general chemistry 01 natural sciences Biochemistry Dimethyl malonate 0104 chemical sciences Enamine Ion chemistry.chemical_compound chemistry Drug Discovery Organic chemistry Catalytic hydrogenation Conjugate |
| Zdroj: | Tetrahedron Letters. 38:1455-1458 |
| ISSN: | 0040-4039 |
| Popis: | Direct addition of dimethyl malonate anion to a 1,4-conjugate iminium salt of 3-ethylindolo[2,3- a ]quinolizidine 4a (regenerated from the corresponding α-aminonitrile 4b ) afforded enamine 5. Catalytic hydrogenation of compound 5 led stereoselectively to compound 6 ( pseudo ), which is the highly desired intermediate for the preparation of several Corynanthe alkaloids, including (±)-hirsutine 7. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect