Related Experiment Video
Updated: May 16, 2025

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Concise Total Syntheses of Leuconoxine-Type Alkaloids Enabled by Palladium/Norbornene-Catalyzed Pyrrole
1Department of Chemistry, University of Chicago, Chicago, Illinois, 60637, USA.
Abstract:
Concise total syntheses of five leuconoxine-type alkaloids, i.e., chloromelodinine, leuconodine A, leuconodine F, melodinine E, and leuconoxine, are achieved through a pyrrole-centered strategy. The approach features a newly developed palladium/norbornene-catalyzed pyrrole double C─H functionalization reaction to generate the core skeleton and a divergent oxidative dearomatization to complete the end game. In addition, no protecting group was employed, and the strategic use of a chloro substituent offers a number of advantages in these syntheses, which could have implications beyond this work. The discovery of an unusual chloro 1,2-migration reaction enabled the first total synthesis of chloromelodinine E. This work represents the shortest syntheses of these natural products to date with 10-11 total steps.
More Related Videos
10:42Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
α-Alkylation of Ketones via Enolate Ions
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation