Work

A Concise Synthesis of Pawhuskin A

Year: 2008

Type: article

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.

Source: Journal of Natural Products

DOI: 10.1021/np800351c

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

Institution: University of Iowa

Language: English

Topic: Phosphorus compounds and reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Cancer Institute, National Institute of Environmental Health Sciences

Awards: G5285655705, G602106545, CENTER FOR RESEARCH ON BOTANICAL DIETARY SUPPLEMENTS