ol0c02188_si_001.pdf (14.2 MB)
Total Synthesis of Ajudazol A by a Modular Oxazole Diversification Strategy
journal contribution
posted on 2020-08-06, 22:20 authored by Philipp Wollnitzke, Sebastian Essig, Jan Philipp Gölz, Karin von Schwarzenberg, Dirk MencheThe 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.