TitleTotal Synthesis of Leuconoxine, Melodinine E, and Mersicarpine through a Radical Translocation–Cyclization Cascade
Publication TypeJournal Article
Year of Publication2019
AuthorsKim R, Ferreira AJ, Beaudry CM
JournalAngewandte Chemie International Edition
Volume58
Pagination12595-12598
Keywordsleuconoxine, 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.

URLhttps://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201907455
DOI10.1002/anie.201907455