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

View/ Open
Issue Date
2013-12-06Author
Riley, Andrew Philip
Day, Victor W.
Navarro, Hernán A.
Prisinzano, Thomas E.
Publisher
American Chemical Society
Type
Article
Article Version
Scholarly/refereed, author accepted manuscript
Rights
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://doi.org/10.1021/ol4027528.
Metadata
Show full item recordAbstract
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.
Collections
Citation
Riley, A. P., Day, V. W., Navarro, H. A., & Prisinzano, T. E. (2013). Palladium-catalyzed Transformations of Salvinorin A, a Neoclerodane Diterpene from Salvia divinorum. Organic Letters, 15(23), 5936–5939. http://doi.org/10.1021/ol4027528
Items in KU ScholarWorks are protected by copyright, with all rights reserved, unless otherwise indicated.
We want to hear from you! Please share your stories about how Open Access to this item benefits YOU.