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 |