Palladium-Catalyzed Transformations of Salvinorin A, a Neoclerodane Diterpene from Salvia divinorum

Riley, A. P., Day, V. W., Navarro, H., & Prisinzano, T. E. (2013). Palladium-Catalyzed Transformations of Salvinorin A, a Neoclerodane Diterpene from Salvia divinorum. Organic Letters, 15(23), 5936-5939. DOI: 10.1021/ol4027528

Transformations that selectively modify the furan ring present in a variety of naturals products would be useful in the synthesis of biological probes but remain largely underexplored. The neoclerodane diterpene salvinorin A, isolated from Salvia divinorum, is an example of a furan-containing natural product. Following selective bromination of salvinorin A, Suzuki-Miyaura and Sonogashira couplings were accomplished in moderate to good yields without hydrolyzing the labile C-2 acetate or altering the stereochemistry of the epimerizable centers