A method for the synthesis of fused 1,2-naphthoquinones, as analogues of biologically active natural terpene quinones, is described. The intermediate polycyclic naphthalenes were prepared by a one-pot palladium-catalysed process from simple alkynes, one of which was made from an optically pure biomass-derived levoglucosenone. The prepared methoxy-substituted naphthalenes were subsequently transformed in one step to 1,2-naphthoquinones by a trivalent-iodine-mediated oxidation. The naphthoquinone products were found to have cytotoxic properties.
- MeSH
- antitumorózní látky chemická syntéza chemie farmakologie MeSH
- buněčné linie MeSH
- léky antitumorózní - screeningové testy MeSH
- lidé MeSH
- molekulární struktura MeSH
- naftochinony chemická syntéza chemie farmakologie MeSH
- proliferace buněk účinky léků MeSH
- viabilita buněk účinky léků MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
A very short three-step approach to trans,trans,trans-2,5-diaryl-3,4-dimethyltetrahydrofuran lignans is reported. The carbon skeleton is assembled in a single step based on an unprecedented tandem reaction consisting of 1,2-addition of aryllithium reagents to α,β-unsaturated aldehydes, ruthenium-catalyzed redox isomerization of the resulting alkoxides to enolates and their dimerization triggered by single electron oxidation. The resulting 2,3-dialkyl-1,4-diketones form with moderate to good d/l-diastereoselectivity and are transformed to the target tetrahydrofuran lignans by reduction and diastereoselective cycloetherification.
- MeSH
- aldehydy chemická syntéza chemie MeSH
- biomimetika MeSH
- cyklizace MeSH
- furany chemická syntéza chemie MeSH
- isomerie MeSH
- katalýza MeSH
- krystalografie rentgenová MeSH
- lignany chemická syntéza chemie MeSH
- molekulární modely MeSH
- oxidace-redukce MeSH
- oxidační párování MeSH
- ruthenium chemie MeSH
- techniky syntetické chemie MeSH
- Publikační typ
- časopisecké články MeSH
