Back to Search
Start Over
A divergent enantioselective strategy for the synthesis of griseusins
- Source :
- Angewandte Chemie (International ed. in English). 54(38)
- Publication Year :
- 2015
-
Abstract
- The first enantioselective total synthesis of griseusin A, griseusin C, 4′-deacetyl-griseusin A, and two non-native counterparts in 11–14 steps is reported. This strategy highlights a key hydroxy-directed C–H olefination of 1-methylene isochroman with an α,β-unsaturated ketone followed by subsequent stereoselective epoxidation and regioselective cyclization to afford the signature tetrahydro-spiropyran ring. Colorectal cancer cell cytotoxicities of the final products highlight the impact of the griseusin tetrahydro-spiropyran ring on bioactivity. As the first divergent enantioselective synthesis, the strategy put forth sets the stage for further griseusin mechanism-of-action and SAR studies.
- Subjects :
- chemistry.chemical_classification
Ketone
Griseusins
Magnetic Resonance Spectroscopy
Stereochemistry
Chemistry
Enantioselective synthesis
Regioselectivity
Total synthesis
Stereoisomerism
General Medicine
General Chemistry
Ring (chemistry)
Catalysis
Article
Cell Line, Tumor
Humans
Stereoselectivity
Griseusin C
Naphthoquinones
Subjects
Details
- ISSN :
- 15213773
- Volume :
- 54
- Issue :
- 38
- Database :
- OpenAIRE
- Journal :
- Angewandte Chemie (International ed. in English)
- Accession number :
- edsair.doi.dedup.....529787438a1a544bbac6811c950988f8