Journal article
Synthesis of nonracemic 3-deoxyschweinfurthin B
Journal of organic chemistry, Vol.70(3), pp.925-931
02/04/2005
DOI: 10.1021/jo048444r
PMID: 15675850
Abstract
Synthesis of nonracemic 3-deoxyschweinfurthin B has been accomplished through a synthetic sequence including a key cascade cyclization of an epoxy olefin. The intermediate epoxide could be prepared as a single enantiomer through an AD-mix-alpha (or AD-mix-beta) oxidation, and the stereochemistry of the epoxide has been shown to control formation of the two additional stereogenic centers created through the cyclization. Synthetic 3-deoxyschweinfurthin B was found to have potent differential activity in the National Cancer Institute's 60 cell line anticancer assay. This represents the first synthesis of the tetracyclic schweinfurthin skeleton, validating our overall synthetic strategy and providing the first schweinfurthin analogue with activity slightly greater than those of the natural products.
Details
- Title: Subtitle
- Synthesis of nonracemic 3-deoxyschweinfurthin B
- Creators
- Jeffrey D Neighbors - Department of Chemistry, University of Iowa, Iowa City, IA 52242-1294, USAJohn A BeutlerDavid F Wiemer
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.70(3), pp.925-931
- DOI
- 10.1021/jo048444r
- PMID
- 15675850
- NLM abbreviation
- J Org Chem
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Publisher
- United States
- Language
- English
- Date published
- 02/04/2005
- Academic Unit
- Neuroscience and Pharmacology; Chemistry
- Record Identifier
- 9983985857202771
Metrics
12 Record Views