Red bee propolis has been utilized in folk medicine for thousands of years to treat a wide range of ailments. Very little is known about the individual constituents of the resin despite the fact that it is widely available in health food stores. Hundreds of compounds have been isolated from Brazilian red bee propolis, including (S)-neovestitol (1) and retusapurpurin A (2). Despite promising preliminary results, biological studies have been limited due to low quantities of both isolated compounds. Accordingly, we have developed syntheses of (S)-neovestitol (1) and retusapurpurin A (2). Our studies determined that the retusapurpurin core could be constructed using a Brønsted acid-promoted annulation. Additionally, the asymmetric synthesis of 1 via a dynamic kinetic resolution process will be described.

Total synthesis of retusapurpurin A via a novel flavylium annulation

ACS Spring 2022

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