A concise synthesis of Pawhuskin A

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

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

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
Volume71
Issue number11
DOIs
StatePublished - Nov 1 2008

Fingerprint

Stilbenes
Organophosphonates
Alkenes
Opioid Receptors
Bioactivity
Biological Products
Aldehydes
Isomers
Condensation
pawhuskin A
In Vitro Techniques

All Science Journal Classification (ASJC) codes

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

Cite this

Neighbors, J., 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
Neighbors, Jeffrey ; Buller, Matthew J. ; Boss, Kelly D. ; Wiemer, David F. / A concise synthesis of Pawhuskin A. In: Journal of Natural Products. 2008 ; Vol. 71, No. 11. pp. 1949-1952.
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Neighbors, J, Buller, MJ, Boss, KD & Wiemer, DF 2008, 'A concise synthesis of Pawhuskin A', Journal of Natural Products, vol. 71, no. 11, pp. 1949-1952. https://doi.org/10.1021/np800351c

A concise synthesis of Pawhuskin A. / Neighbors, Jeffrey; Buller, Matthew J.; Boss, Kelly D.; Wiemer, David F.

In: Journal of Natural Products, Vol. 71, No. 11, 01.11.2008, p. 1949-1952.

Research output: Contribution to journalArticle

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