Total Synthesis of Ajudazol A by a Modular Oxazole Diversification Strategy

Wollnitzke, Philipp; Essig, Sebastian; Goelz, Jan Philipp; Schwarzenberg, Karin von und Menche, Dirk (2020): Total Synthesis of Ajudazol A by a Modular Oxazole Diversification Strategy. In: Organic Letters, Bd. 22, Nr. 16: S. 6344-6348

Abstract

The total synthesis of the potent respiratory chain inhibitor ajudazol A was accomplished by a concise strategy in 17 steps (longest linear sequence). The modular approach was based on a direct oxazole functionalization strategy involving a halogen dance reaction for selective halogenation in combination with a challenging combination of sp(2)-sp(2) and sp(2)-sp(3) Negishi cross coupling reactions. The applicability of this strategy for analogue synthesis was demonstrated by the synthesis of a simplified as well as stabilized ajudazol analogue.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department für Pharmazie - Zentrum für Pharmaforschung
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 1523-7060
• Sprache: Englisch