Journal article
Synthesis of indole analogues of the natural schweinfurthins
Journal of organic chemistry, Vol.78(18), pp.9291-9302
09/20/2013
DOI: 10.1021/jo4014244
PMCID: PMC3940163
PMID: 24004185
Abstract
An interest in the schweinfurthins, natural stilbenes with significant antiproliferative activity, has prompted efforts to prepare a set of indole analogues. To approach the desired compounds through a Horner-Wadsworth-Emmons condensation, new indole derivatives bearing a phosphonomethyl substituent in the B-ring were required. The parent indole system with the necessary substitution pattern was obtained through Stobbe condensation and cyclization. A prenyl substituent was incorporated at the C3 position of a 4,6-disubstituted indole through a highly regioselective electrophilic aromatic substitution reaction, while metalation and alkylation provided the C2-prenylated indole. After introduction of the phosphonate group through classical reactions, the new indole phosphonates were found to undergo the desired condensation with nonracemic aldehydes representing the schweinfurthin left half. This approach provides facile access to new heteroaromatic analogues of the natural schweinfurthins and should be applicable to many other natural stilbenes as well.
Details
- Title: Subtitle
- Synthesis of indole analogues of the natural schweinfurthins
- Creators
- John G Kodet - Department of Chemistry, University of Iowa , Iowa City, Iowa 52242-1294, United StatesDavid F Wiemer
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.78(18), pp.9291-9302
- DOI
- 10.1021/jo4014244
- PMID
- 24004185
- PMCID
- PMC3940163
- NLM abbreviation
- J Org Chem
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Publisher
- American Chemical Society (ACS); United States
- Grant note
- R41 CA126020 / NCI NIH HHS R41CA126020 / NCI NIH HHS
- Language
- English
- Date published
- 09/20/2013
- Academic Unit
- Neuroscience and Pharmacology; Chemistry
- Record Identifier
- 9983985802702771
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