AI Article Synopsis
- - Polycyclic polyprenylated acylphloroglucinols (PPAPs) are over 400 natural compounds known for their diverse bioactivities, including properties that may help with depression, infections, obesity, and cancer.
- - Researchers developed a new method to synthesize cyclic β-prenyl ketones, which are crucial for creating various PPAPs with high purity and selectivity using a chiral copper catalyst and an organoborate reagent, completing reactions in minutes at room temperature.
- - This method enables the production of enantiomerically pure precursors for PPAPs more efficiently, highlighted by successful syntheses of nemorosonol and its conversion to garcibracteatone in
Article Abstract
Polycyclic polyprenylated acylphloroglucinols (PPAPs) are a class of >400 natural products with a broad spectrum of bioactivity, ranging from antidepressant and antimicrobial to anti-obesity and anticancer activity. Here, we present a scalable, regio-, site-, and enantioselective catalytic method for synthesis of cyclic β-prenyl ketones, compounds that can be used for efficient syntheses of many PPAPs in high enantiomeric purity. The transformation is prenyl conjugate addition to cyclic β-ketoesters promoted by a readily accessible chiral copper catalyst and involving an easy-to-prepare and isolable organoborate reagent. Reactions reach completion in just a few minutes at room temperature. The importance of this advance is highlighted by the enantioselective preparation of intermediates previously used to generate racemic PPAPs. We also present the enantioselective synthesis of nemorosonol (14 steps, 20% yield) and its one-step conversion to another PPAP, garcibracteatone (52% yield).
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| http://dx.doi.org/10.1126/science.adr8612 | DOI Listing |
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