Biomimetic total synthesis of (±)-yezo'otogirin AElectronic supplementary information (ESI) available. See DOI: 10.1039/c4ob00186a

• Main Authors: Lam, Hiu C, Kuan, Kevin K. W, George, Jonathan H
• Format: Article
• Language: English
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/c4ob00186a

The total synthesis of yezo'otogirin A has been achieved via a biosynthetically-inspired strategy. Diastereoselective synthesis of pre-yezo'otogirin A, the proposed biosynthetic pre-cursor of yezo'otogirin A, was accomplished in eight steps from 3-ethoxy-2-cyclohexenone. A biomimetic oxidative radical cyclization was then used to construct the unique tricyclic ring system of yezo'otogirin A. The synthesis showcases the ability of biomimetic radical cyclizations to generate complex natural products from unprotected intermediates. A concise total synthesis of (±)-yezo'otogirin A has been achieved via its presumed biosynthetic precursor using a late-stage biomimetic oxidative radical cyclization.