OREGON STATE UNIVERSITY
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| Title | Total Synthesis of Leuconoxine, Melodinine E, and Mersicarpine through a Radical Translocation–Cyclization Cascade |
| Publication Type | Journal Article |
| Year of Publication | 2019 |
| Authors | Kim R, Ferreira AJ, Beaudry CM |
| Journal | Angewandte Chemie International Edition |
| Volume | 58 |
| Pagination | 12595-12598 |
| Keywords | leuconoxine, melodinine E, mersicarpine, radical reactions, total synthesis |
| Abstract | Abstract The Aspidosperma alkaloids leuconoxine, melodinine E, and mersicarpine were synthesized. The approach features a key cascade radical reaction. A 1,5-hydrogen atom transfer is followed by spontaneous 5-exo-trig cyclization to construct the central indoline architecture. Late-stage differentiation of the radical cyclization product by chemoselective oxidation allows production of either the leuconoxine/melodinine E or mersicarpine structure. |
| URL | https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201907455 |
| DOI | 10.1002/anie.201907455 |