Related Experiment Video
Updated: May 19, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Radical-mediated dimerization and oxidation reactions for the synthesis of complex alkaloids
Stephen P Lathrop1, Justin Kim, Mohammad Movassaghi
1Massachusetts Institute of Technology, Departement of Chemistry, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, USA.
Abstract:
Concise and general strategies for radical-based dimerization of cyclotryptamine and cyclotryptophan derivatives in addition to radical-based oxidation of structurally complex diketopiperazines are discussed. The impact of these radical-based chemistries on the rapid generation of molecular complexity is highlighted using representative examples from recent complex homodimeric alkaloid total syntheses. Additionally, a new and general strategy for radical-based directed heterodimerization of cyclotryptamine substructures via solvent-caged unsymmetrical diazene fragmentation is discussed.
More Related Videos
09:54Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
Related Concept Videos
Radical Reactivity: Overview
Radical Oxidation of Allylic and Benzylic Alcohols
Radical Reactivity: Nucleophilic Radicals
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Radical Formation: Addition
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an unpaired...
Radical Formation: Elimination