Journal article
Selective Prenylation of Protected Phenols for Synthesis of Pawhuskin A Analogues
Journal of organic chemistry, Vol.81(4), pp.1585-1592
02/19/2016
DOI: 10.1021/acs.joc.5b02756
PMID: 26771823
Abstract
Pawhuskin A is a prenylated stilbene that functions as an antagonist of the kappa opioid receptor. Analogues of this natural product bearing different placements of the prenyl group in the A-ring have shown selectivity for either the kappa or the delta receptors subtypes. This differential activity has drawn attention to regiospecific preparation of the C-2, C-5, and C-6 prenylated A-ring regioisomers. Through halogen metal exchange, advanced intermediates representing each of these regioisomers have been prepared, and the new C-6 intermediate has been converted to a new analogue of the natural stilbene.
Details
- Title: Subtitle
- Selective Prenylation of Protected Phenols for Synthesis of Pawhuskin A Analogues
- Creators
- Kevyn D Gardner - Department of Chemistry, University of Iowa , Iowa City, Iowa 52242-1294, United StatesDavid F Wiemer - Department of Chemistry, University of Iowa , Iowa City, Iowa 52242-1294, United States
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.81(4), pp.1585-1592
- DOI
- 10.1021/acs.joc.5b02756
- PMID
- 26771823
- NLM abbreviation
- J Org Chem
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Publisher
- United States
- Grant note
- DOI: 10.13039/100001024, name: Roy J. Carver Charitable Trust, award: 01-224
- Language
- English
- Date published
- 02/19/2016
- Academic Unit
- Neuroscience and Pharmacology; Chemistry
- Record Identifier
- 9983985825902771
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