Palladium-catalyzed transformations of salvinorin A, a neoclerodane diterpene from Salvia divinorum.
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.
Departments of Chemistry and Medicinal Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7572, United States , and Research Triangle Institute , Research Triangle Park, North Carolina 27709, United States.
Andrew P
AP
Riley
Victor W
VW
Day
Hernán A
HA
Navarro
Thomas E
TE
Prisinzano
D001688:Biological Products / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D045785:Diterpenes, Clerodane / Q000737:chemistry*; D005663:Furans / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D027544:Salvia / Q000737:chemistry*
D001688:Biological Products; D045785:Diterpenes, Clerodane; D005663:Furans; D010165:Palladium; C090499:salvinorin A