Total Synthesis of Ajudazol A by a Modular Oxazole Diversification Strategy

Wollnitzke, Philipp; Essig, Sebastian; Goelz, Jan Philipp; Schwarzenberg, Karin von; Menche, Dirk (2020): Total Synthesis of Ajudazol A by a Modular Oxazole Diversification Strategy. In: Organic Letters, Vol. 22, No. 16: pp. 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.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Pharmacy
• Subjects: 500 Science > 540 Chemistry
• ISSN: 1523-7060
• Language: English