Centrolobine is a natural product originally isolated from the stem of Brosimum potabile and the heartwood of Centrolobium robustum. Because of its anti-parasitic, antifungal, and antibiotic properties, the synthesis of centrolobine has sparked the interest of many synthetic chemists. Our synthetic approach to centrolobine hinges on a gold(I)-catalyzed etherification. Synthesis of (2E)-7-(4-methoxyphenyl)hept-2-ene-1,7-diol and its reaction with gold catalysts to form the tetrahydropyran core of centrolobine will be presented.

Studies on the synthesis of centrolobine

243rd National Meeting (2012)

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