Concise Total Syntheses of Leuconoxine‐Type Alkaloids Enabled by Palladium/Norbornene‐Catalyzed Pyrrole Difunctionalization
Year: 2025
Type: article
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.
Source: Angewandte Chemie
Institution: University of Chicago
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $5,790
Award: G486742774
OpenAlex ID: W4409001496