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Total Synthesis of Ajudazol A by a Modular Oxazole Diversification Strategy

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journal contribution
posted on 06.08.2020 by Philipp Wollnitzke, Sebastian Essig, Jan Philipp Gölz, Karin von Schwarzenberg, Dirk Menche
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 sp2–sp2 and sp2–sp3 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.