Total Synthesis of Icumazole A Using a Modified Cadiot-Chodkiewicz Coupling
Jack Buntine1, Samrat Dasgupta1, Keely Dorney1
1School of Chemistry, The Bio21 Institute, The University of Melbourne, Melbourne, Victoria 3010, Australia.
Abstract:
The first total synthesis of myxobacteria metabolite icumazole A (1) is reported. Key steps in the route include an organocatalyzed asymmetric self-aldol reaction followed by an acetate aldol reaction to form the stereotriad present in the oxazole moiety, an intramolecular Diels-Alder reaction to form the isochromanone, and an acetylide addition and selective methylation. The final steps involved a high-yielding modified Cadiot-Chodkiewicz coupling and stereoselective reduction to secure the Z,Z-diene and afford 1.
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