ArticleThe Journal of organic chemistry2011
Exploration of cascade cyclizations terminated by tandem aromatic substitution: total synthesis of (+)-schweinfurthin A.
Article in The Journal of organic chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Substitution of a triazole for the central olefin in biologically active stilbenes.Bioorganic & medicinal chemistry letters · 2022Article
- RNAseq reveals extensive metabolic disruptions in the sensitive SF-295 cell line treated with schweinfurthins.Scientific reports · 2022Article
- Synthesis of a Coumarin-Based Analogue of Schweinfurthin F.The Journal of organic chemistry · 2021Article
- Schweinfurthins A-Q: isolation, synthesis, and biochemical properties.RSC advances · 2018Review
- Synthesis of amide isosteres of schweinfurthin-based stilbenes.Bioorganic & medicinal chemistry · 2017Article
- Article
- A selective delta opioid receptor antagonist based on a stilbene core.Bioorganic & medicinal chemistry letters · 2015Article
- Synthesis and structure activity relationships of schweinfurthin indoles.Bioorganic & medicinal chemistry · 2014Article
- Stilbenes as κ-selective, non-nitrogenous opioid receptor antagonists.Journal of natural products · 2014Article
- Electrophilic aromatic prenylation via cascade cyclization.Tetrahedron · 2013Article
- Synthesis of indole analogues of the natural schweinfurthins.The Journal of organic chemistry · 2013Article
- Relevance of the C-5 position to schweinfurthin induced cytotoxicity.Bioorganic & medicinal chemistry · 2011Article
- Direct conversion of benzylic and allylic alcohols to phosphonates.The Journal of organic chemistry · 2011Article
- First total synthesis of (+)-Vedelianin, a potent antiproliferative agent.Tetrahedron letters · 2011Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
The termination of epoxide-initiated cascade cyclizations with a range of "protected" phenols is described. When the protecting group can be lost as a stabilized electrophile, the cascade process continues beyond ring closure to afford products which have undergone a tandem electrophilic aromatic substitution. A number of groups have proven viable in this process and the regiochemistry of their substitution reactions has been studied. Application of this methodology in the first total synthesis of (+)-schweinfurthin A, a potent antiproliferative agent, has been achieved.
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Registered trials
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