Expedient pyrrolizidine synthesis by propargylsilane addition to N-acyliminium ions followed by gold-catalyzed α-allenyl amide cyclization
| Authors |
|
|---|---|
| Publication date | 2009 |
| Journal | Journal of Organic Chemistry |
| Volume | Issue number | 74 | 16 |
| Pages (from-to) | 6327-6330 |
| Organisations |
|
| Abstract | A reaction sequence, involving the addition of (substituted) propargylsilanes to lactate-derived N-acyliminium ions followed by gold-catalyzed cyclization of the resulting alpha-allenyl amide, is applied in expedient syntheses of pyrrolizidine alkaloids heliotridine and ent-retronecine in five steps from (S)-malic acid. |
| Document type | Article |
| Language | English |
| Published at |
https://doi.org/10.1021/jo901393y
(Final published version)
|
| Permalink to this page | |