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Practical Stereoselective Synthesis of Eribulin Fragment toward Building a Hybrid Macrocyclic Toolbox
- Source :
- Organic Letters. 17:468-471
- Publication Year :
- 2015
- Publisher :
- American Chemical Society (ACS), 2015.
-
Abstract
- A practical stereoselective synthesis to obtain the substituted furan ring as the substructure of eribulin is developed. An asymmetric syn-aldol and intramolecular oxy-Michael were two key steps in our approach. The functionalized furan derivatives were then utilized further to build the 14- and 12-membered macrocyclic diversity as trans- and cis-fused (C-29 and C-30) compounds. This is the first report of building a chemical toolbox with macrocyclic small molecules having trans- or cis-fused 14- or 12-membered rings containing the substructure of eribulin and its diastereomer.
- Subjects :
- Aldehydes
Macrocyclic Compounds
Molecular Structure
Stereochemistry
Organic Chemistry
Diastereomer
Stereoisomerism
Ketones
Ring (chemistry)
Biochemistry
Small molecule
Combinatorial chemistry
chemistry.chemical_compound
chemistry
Fragment (logic)
Cyclization
Intramolecular force
Furan
Stereoselectivity
Physical and Theoretical Chemistry
Furans
Eribulin
Subjects
Details
- ISSN :
- 15237052 and 15237060
- Volume :
- 17
- Database :
- OpenAIRE
- Journal :
- Organic Letters
- Accession number :
- edsair.doi.dedup.....6948e8f9f012ef55f3c8166cabfb719f