Tandem Radical Cyclizations Leading to Indolizidinones and Pyrrolizidinones. -Depending on the alkene substituent, dehydroamino esters (I), (III), and (V) undergo 5-endo-5-exo or 5-endo-6-endo tandem cyclization under radical conditions with tin hydrides. Bicyclic products having potential applicat
Tandem radical cyclisations leading to indolizidinones and pyrrolizidinones
✍ Scribed by S. Richard Baker; Andrew F. Parsons; Jean-François Pons; Michelle Wilson
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 238 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
Reaction of various dehydroamino esters with tin hydrides resulted in 5-endo-5-exo or 5-endo-6endo tandem cyclisafion reactions. The preferred pathway was dependent on alkene substitution and the bicyclic products have potential application in indolizidine and pyrrolizidine alkaloid synthesis.
📜 SIMILAR VOLUMES
The copper(I) or ruthenium(II)-mediated radical cyclisation of halo-amides has been utilised to afford functionalised pyrrolidinones via 5-endo-trig or 5-exo-trig radical cyclisation pathways. This methodology has been applied to novel and concise syntheses of the anti-epileptic drug gabapentin and