Abstract
A modular, 18-step total synthesis of hyperforin is described. The natural product was quickly accessed using latent symmetry elements, whereby a group-selective, Lewis acid-catalyzed epoxide-opening cascade cyclization was used to furnish the bicyclo[3.3.1]nonane core and set two key quaternary stereocenters.
Highlights
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The therapeutic potential of hyperforin is severely handicapped by its poor water solubility, facile oxidative degradation upon exposure to light and air,[6] and potent activation of pregnane X receptor,[7] leading to increased expression of many genes involved in xenobiotic metabolism
Summary
The Harvard community has made this article openly available. Please share how this access benefits you. Journal of the American Chemical Society 135, no. 2: 644–647
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