Intramolecular difunctionalization of alkynes involving cascade radical 1,4-heteroaryl migrations and formal total synthesis of a β-imidazolyl-γ-lactam alkaloid: isoanantine
Abstract
-methylpyrrole. These cascade radical reactions were used to produce key molecules with two linked heterocycles through a single bond. One of the heterocycles is an unsaturated-γ-lactam and the other is a nitrogen-containing heteroaromatic positioned at the β-carbon of this lactam. Eight key molecules were constructed through this novel transformation in low-to-satisfactory yields (11-72%). A structure-reactivity relationship is also provided herein. This report is the first to describe an intramolecular difunctionalization of alkynes involving the migration of various nitrogen-containing heteroaryl groups. Novel skeletons such as these are usually found in natural products or in potential drug candidates, and it is noteworthy that the conversion of an unsaturated-β-imidazolyl-γ-lactam to a natural product, isoanantine, was also achieved through formal total synthesis.
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Radical Photochemical Reactions
Advanced Synthetic Organic Chemistry
Publication details
- Journal / source
- Organic & Biomolecular Chemistry
- Publisher
- Royal Society of Chemistry (RSC)
- Volume
- 24
- Issue
- 21
- Pages
- 4488–4494
- Publication date
- 1 January 2026
- Language
- EN