Journal article
Exploration of cascade cyclizations terminated by tandem aromatic substitution: total synthesis of (+)-schweinfurthin A
Journal of organic chemistry, Vol.76(3), pp.909-919
02/04/2011
DOI: 10.1021/jo1022102
PMCID: PMC3069933
PMID: 21226493
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.
Details
- Title: Subtitle
- Exploration of cascade cyclizations terminated by tandem aromatic substitution: total synthesis of (+)-schweinfurthin A
- Creators
- Joseph J Topczewski - Department of Chemistry, University of Iowa, Iowa City, 52242-1294, USAJohn G KodetDavid F Wiemer
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.76(3), pp.909-919
- DOI
- 10.1021/jo1022102
- PMID
- 21226493
- PMCID
- PMC3069933
- NLM abbreviation
- J Org Chem
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Publisher
- United States
- Grant note
- R41 CA126020 / NCI NIH HHS R41 CA126020-01 / NCI NIH HHS R41CA126020 / NCI NIH HHS
- Language
- English
- Date published
- 02/04/2011
- Academic Unit
- Neuroscience and Pharmacology; Chemistry
- Record Identifier
- 9983985874302771
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