A concise synthesis of pawhuskin A

Jeffrey D Neighbors; Matthew J Buller; Kelly D Boss; David F Wiemer

doi:10.1021/np800351c

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Journal article

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A concise synthesis of pawhuskin A

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

Journal of natural products (Washington, D.C.), Vol.71(11), pp.1949-1952

11/2008

DOI: 10.1021/np800351c

PMCID: PMC6679901

PMID: 18922035

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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.

Terpenes - chemistry

Fabaceae - chemistry

Stereoisomerism

Stilbenes - chemical synthesis

Molecular Structure

Stilbenes - chemistry

Terpenes - chemical synthesis

Details

Title: Subtitle: A concise synthesis of pawhuskin A
Creators: Jeffrey D Neighbors - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242-1294, USA
Matthew J Buller
Kelly D Boss
David F Wiemer
Resource Type: Journal article
Publication Details: Journal of natural products (Washington, D.C.), Vol.71(11), pp.1949-1952
DOI: 10.1021/np800351c
PMID: 18922035
PMCID: PMC6679901
NLM abbreviation: J Nat Prod
ISSN: 0163-3864
eISSN: 1520-6025
Publisher: United States
Grant note: 2 T32 CA79445 / NCI NIH HHS P01 ES012020 / NIEHS NIH HHS
Language: English
Date published: 11/2008
Academic Unit: Neuroscience and Pharmacology; Chemistry
Record Identifier: 9983985839402771

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