Journal
ORGANIC LETTERS
Volume 15, Issue 23, Pages 5936-5939Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol4027528
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Funding
- National Institute on Drug Abuse [DA018151]
- NIH Dynamic Aspects of Chemical Biology training grant [GM008545]
- National Science Foundation [CHE-0923449]
- University of Kansas
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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.
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