A concise synthesis of Pawhuskin A

Jeffrey D. Neighbors, Matthew J. Buller, Kelly D. Boss, David F. Wiemer

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Pawhuskin A is an isoprenylated stilbene that was isolated from Dalea purpurea and reported to have affinity for the opioid receptor in vitro. It has been synthesized through a convergent sequence that joins a prenylated aldehyde with a geranylated phosphonate in a stereoselective Horner-Wadsworth-Emmons condensation to afford the target E olefin isomer. This synthesis confirms the structure assigned to the natural product and establishes a route that may be used to explore its biological activity and to prepare more active analogues.

Original languageEnglish (US)
Pages (from-to)1949-1952
Number of pages4
JournalJournal of Natural Products
Issue number11
StatePublished - Nov 1 2008

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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    Neighbors, J. D., Buller, M. J., Boss, K. D., & Wiemer, D. F. (2008). A concise synthesis of Pawhuskin A. Journal of Natural Products, 71(11), 1949-1952. https://doi.org/10.1021/np800351c