Enantioselective total synthesis of the indole alkaloid 16-episilicine.
The first total synthesis of (-)-16-episilicine has been completed from a phenylglycinol-derived bicyclic lactam, the key steps being stereoselective conjugate addition and alkylation reactions, and a ring-closing metathesis.
2-Formyl-3-Methoxymethylindole, 3-Ethoxymethyl-2-Formylindole and 2-Formyl-3-Methylindole
Abstract Base-catalysed hydrolysis of 2-formyl-3-methyl-1-phenyl-sulphonylindole results in the formation of 3-alkoxy-methyl-2-formylindoles. Cleavage of the 1-phenyl-sulphonyl group with sodium amalgam produces 2-hydroxymethyl-3-methylindole.
Synthesis and 5HT modulating activity of stereoisomers of 3-phenoxymethyl-4-phenylpiperidines.
A series of pairs of enantiomers of substituted 3-phenoxymethyl-4-phenylpiperidines has been prepared from arecoline or alpha-methylstyrene by a combination of stereospecific reactions and optical resolutions. The ability of the compounds to modulate serotonin (5HT) neurotransmission in vitro was determined. Several derivatives, among which is the antidepressant paroxetine, are very potent inhibitors of 5HT reuptake. These compounds exhibit a pronounced steric requirement for inhibition of 5HT reuptake and binding to 5HT2A and 5HT2C receptors.