Enantioselective Total Synthesis of (+)-Gephyrotoxin 287C
A synthesis of (+)-gephyrotoxin 287C using, (S)-phenylglycinol-derived tricyclic lactam 7 as the starting enantiomeric scaffold is reported. From the stereochemical standpoint, the key steps are the generation of the DHQ C-5 stereocenter by hydrogenation of the C-C double bond, removal of the chiral...
| Authors: | , , , , |
|---|---|
| Format: | article |
| Status: | Versión aceptada para publicación |
| Publication Date: | 2017 |
| Country: | España |
| Institution: | Universidad de Barcelona |
| Repository: | Dipòsit Digital de la UB |
| OAI Identifier: | oai:diposit.ub.edu:2445/127597 |
| Online Access: | https://hdl.handle.net/2445/127597 |
| Access Level: | Open access |
| Keyword: | Síntesi asimètrica Lactames Catàlisi asimètrica Asymmetric synthesis Lactams Enantioselective catalysis |
| Summary: | A synthesis of (+)-gephyrotoxin 287C using, (S)-phenylglycinol-derived tricyclic lactam 7 as the starting enantiomeric scaffold is reported. From the stereochemical standpoint, the key steps are the generation of the DHQ C-5 stereocenter by hydrogenation of the C-C double bond, removal of the chiral inductor to give a cis-DHQ introduction of the DHQ C-2 substituent, completion of the (Z)-enyne moiety, and generation of the C-1 stereocenter during closure of the pyrrolidine ring. |
|---|