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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
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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.