Synthetic studies of neoclerodane diterpenes from Salvia divinorum: Exploration of the 1-position

Kenneth G. Holden, Kevin Tidgewell, Alfred Marquam, Richard B. Rothman, Hernán Navarro, Thomas E. Prisinzano

Research output: Contribution to journalArticlepeer-review

26 Scopus citations


Modification of the C-1 ketone of salvinorin A (2a) produces analogues with opioid antagonist properties. Of particular significance is the finding that 1-deoxo-1,10-dehydrosalvinorin A (11a) is a moderately potent antagonist at all three opioid receptor subtypes, and that herkinorin (2b), a μ agonist, is converted to a weak antagonist by removal of the C-1 ketone (3b and 11b). These observations suggest that the ketone of 2b is a key structural feature responsible for μ agonist activity.

Original languageEnglish
Pages (from-to)6111-6115
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Issue number22
StatePublished - Nov 15 2007

Bibliographical note

Funding Information:
This work was supported by National Institutes of Health, National Institute on Drug Abuse Grant DA018151 (to T.E.P.). The authors also thank Keith Warner for technical assistance and the American Foundation for Pharmaceutical Education (K.T.) and the University of Iowa Graduate College (A.M.) for predoctoral fellowships.


  • Antagonist
  • Opioid
  • Salvia divinorum
  • Salvinorin A
  • κ

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry


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