Work

Asymmetric Synthesis of the Pentacyclic Framework of Kopsia Alkaloids

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide Pyrroloazocine alkaloids from the Kopsia genus exhibit structural complexity and pharmacological potential. We report the concise and asymmetric synthesis of a pentacyclic core from l -proline. The key features include a C–N–C chirality transfer process to prepare the α-tertiary amine intermediate enantioselectively, an eight-membered C ring-forming Friedel–Crafts reaction at the indole C3 position, and a dearomative indole–Claisen rearrangement to form a bridged pentacyclic scaffold. This study provides a versatile platform for the divergent synthesis of diverse Kopsia alkaloids.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c03771

Authors: Yeonghun Song, John Park, Sanghee Kim

Institution: Seoul National University

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: National Research Foundation, Seoul National University, National Research Foundation of Korea, Ministry of Science and ICT, South Korea