BIOMAT Database Logo BIOMAT Database Logo

Total Synthesis of Leuconoxine, Melodinine E, and Mersicarpine through a Radical Translocation-Cyclization Cascade. 2019

Ryan Kim, and Andrew J Ferreira, and Christopher M Beaudry
Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, OR, 97333, USA.

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.

UI MeSH Term Description Entries

Related Publications

Ryan Kim, and Andrew J Ferreira, and Christopher M Beaudry
Unified enantioselective total syntheses of (-)-scholarisine G, (+)-melodinine E, (-)-leuconoxine and (-)-mersicarpine.
March 2019, Chemical communications (Cambridge, England),
Ryan Kim, and Andrew J Ferreira, and Christopher M Beaudry
A photoinduced cyclization cascade-total synthesis of (-)-leuconoxine.
April 2015, Chemistry (Weinheim an der Bergstrasse, Germany),
Ryan Kim, and Andrew J Ferreira, and Christopher M Beaudry
Biosynthetically inspired divergent approach to monoterpene indole alkaloids: total synthesis of mersicarpine, leuconodines B and D, leuconoxine, melodinine E, leuconolam, and rhazinilam.
December 2014, Organic letters,
Ryan Kim, and Andrew J Ferreira, and Christopher M Beaudry
Total synthesis of mersicarpine through a cationic cyclization approach.
March 2014, Organic letters,
Ryan Kim, and Andrew J Ferreira, and Christopher M Beaudry
Total synthesis of (±)-mersicarpine following a 6-exo-trig radical cyclization.
August 2022, Organic & biomolecular chemistry,
Ryan Kim, and Andrew J Ferreira, and Christopher M Beaudry
Total Synthesis of Sculponin U through a Photoinduced Radical Cascade Cyclization.
July 2023, Angewandte Chemie (International ed. in English),
Ryan Kim, and Andrew J Ferreira, and Christopher M Beaudry
Total Synthesis of (-)-Histrionicotoxin through a Stereoselective Radical Translocation-Cyclization Reaction.
January 2017, Angewandte Chemie (International ed. in English),
Ryan Kim, and Andrew J Ferreira, and Christopher M Beaudry
Total Syntheses of (-)-Mersicarpine, (-)-Scholarisine G, (+)-Melodinine E, (-)-Leuconoxine, (-)-Leuconolam, (-)-Leuconodine A, (+)-Leuconodine F, and (-)-Leuconodine C: Self-Induced Diastereomeric Anisochronism (SIDA) Phenomenon for Scholarisine G and Leuconodines A and C.
May 2015, Journal of the American Chemical Society,
Ryan Kim, and Andrew J Ferreira, and Christopher M Beaudry
Total Synthesis of (-)-Lepadiformine A via Radical Translocation-Cyclization Reaction.
May 2020, Organic letters,
Ryan Kim, and Andrew J Ferreira, and Christopher M Beaudry
Enantioselective total syntheses of leuconolam-leuconoxine-mersicarpine group monoterpene indole alkaloids.
December 2013, Journal of the American Chemical Society,
Copied contents to your clipboard!