ABSTRACT
An enantioselective synthesis of the phenyl ring-containing strioglactone, (-)-solanocol, is described. Application of a Dynamic Kinetic Resolution (DKR) in the stereo-defining step enabled a step-economical synthesis to be achieved, and allowed access to natural and non-natural enantiomers with equal facility. Results of seed germination assays and Differential Scanning Fluorimetry (DSF) measurements with the known strigolactone receptor protein, Decreased Apical Dominance 2 (DAD2), are reported.
ABSTRACT
In contrast to a biomimetic electrophilic cyclisation cascade, we employ a contra-biomimetic nucleophilic cyclisation cascade to give the tricyclic core of 4-hydroxy-GR24 in a single step. Kinetic resolution using a stereoselective Noyori transfer hydrogenation enables the concise synthesis of any enantiomerically enriched 4-hydroxy-GR24 stereoisomer.
ABSTRACT
The total synthesis of a number of carbazolo-1,4-quinone natural products using on-water chemistry is described. A recently developed domino 'in-water, on-water' process is employed to rapidly and efficiently generate königinequinone A, which subsequently enables access to murrayaquinones B, C, D and E, and pyrayaquinones B and C, via a remarkably facile on-water catalysed Claisen rearrangement.
Subject(s)
Biological Products/chemical synthesis , Carbazoles/chemical synthesis , Quinones/chemical synthesis , Water/chemistry , Biological Products/chemistry , Carbazoles/chemistry , Catalysis , Quinones/chemistry , StereoisomerismABSTRACT
Excessive stimulation of NMDA receptors is involved in various CNS pathologies such as Parkinson's disease, acute and chronic pain and cerebral ischaemia. The use of NMDA antagonists as therapeutic agents has been restricted as a result of unwanted side effects including hallucinations and loss of co-ordination. NR2B subtype selective antagonists have previously shown a therapeutic effect without causing the side effects of broad spectrum NMDA antagonists. Considerable research has since been devoted to the development of orally bioavailable, selective NR2B antagonists and their applications in various neurological diseases. The improved therapeutic index of these compounds is expected to be the result of the subtype selectivity and cellular location of the NR2B receptors within the CNS. This review describes recent advances in the development of NR2B antagonists as well as their therapeutic applications.
