Unified approach to indolosesquiterpene alkaloids: total syntheses of anti-viral agents, xiamycin A and oridamycin A
Abstract
A unified catalytic asymmetric total synthesis of naturally occurring anti-viral indolosesquiterpene alkaloids, xiamycin A (1a) and oridamycin A (2a), has been accomplished. The In(III)-catalyzed regio- and diastereoselective ene-yne cyclization has been utilized to construct the pentacyclic skeleton 6 (>20 : 1 dr) having an exocyclic olefin. Diastereoselective hydroboration oxidation afforded the advanced intermediate β-hydroxy aldehyde 5a. Finally, a late-stage highly diastereoselective methylation followed by stereocenter adjustment completed the total synthesis of xiamycin A (1a) and oridamycin A (2a).
Fields of Study & Subjects
Advanced Synthetic Organic Chemistry
Asymmetric Synthesis and Catalysis
Organic Chemistry Synthesis Methods
Publication details
- Journal / source
- Chemical Communications
- Volume
- 62
- Issue
- 15
- Pages
- 4579–4582
- Publication date
- 1 January 2026
- Language
- EN