Palladium-catalyzed transformations of salvinorin A, a neoclerodane diterpene from Salvia divinorum

Andrew P. Riley, Victor W. Day, Hernán A. Navarro, Thomas E. Prisinzano

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)5936-5939
Number of pages4
JournalOrganic Letters
Volume15
Issue number23
DOIs
StatePublished - Dec 6 2013

Funding

FundersFunder number
National Institute on Drug AbuseDA018151
National Institutes of Health (NIH)
National Science Foundation (NSF)CHE-0923449
National Institute on Drug AbuseR01DA018151

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

    Fingerprint

    Dive into the research topics of 'Palladium-catalyzed transformations of salvinorin A, a neoclerodane diterpene from Salvia divinorum'. Together they form a unique fingerprint.

    Cite this