Evolution of a Polyene Cyclization Cascade for the Total Synthesis of (-)-Cyclosmenospongine

Speck, Klaus und Magauer, Thomas (2017): Evolution of a Polyene Cyclization Cascade for the Total Synthesis of (-)-Cyclosmenospongine. In: Chemistry-A European Journal, Bd. 23, Nr. 5: S. 1157-1165

Abstract

We report a full account on the development of a unique cationic polyene cyclization for the total synthesis of the tetracyclic meroterpenoid (-)-cyclosmenospongine. A highly convergent three-component coupling strategy enabled rapid access to individual cyclization precursors that were tested for their reactivity. The successful transformation generates three rings and sets four consecutive stereocenters in a single operation proceeding in a highly efficient manner to give exclusively the trans-decalin framework. In addition, we found that the enol ether geometry and the relative configuration of C3 and C8 are crucial for the success of the polyene cyclization.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 0947-6539
• Sprache: Englisch