Unified approach to fused and spirocyclic oxindoles through lewis-acid-promoted opening of spiroepoxyoxindoles with allylsilanes: application to the formal synthesis of (+/-)-physovenine
| Title | Unified approach to fused and spirocyclic oxindoles through lewis-acid-promoted opening of spiroepoxyoxindoles with allylsilanes: application to the formal synthesis of (+/-)-physovenine |
| Publication Type | Journal Article |
| Year of Publication | 2017 |
| Authors | Sharma, BM, Yadav, M, Gonnade, RG, Kumar, P |
| Journal | European Journal of Organic Chemistry |
| Issue | 18 |
| Pagination | 2603-2609 |
| Date Published | MAY |
| Type of Article | Article |
| ISSN | 1434-193X |
| Keywords | alkaloids, Allylation, annulation, Lewis acids, spiro compounds |
| Abstract | A protocol for the construction of oxindoles containing all-carbon quaternary centres in a highly regioselective manner has been developed. The reaction involves opening of spiroepoxyoxindoles with allylsilanes to give Hosomi-Sakurai-type products as well as new silicon-containing spirocyclic oxindoles. A formal synthesis of (+/-)-physovenine was accomplished in five steps using this protocol. |
| DOI | 10.1002/ejoc.201700259 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.882 |
Divison category:
Physical and Materials Chemistry