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4. 218 Treatment of 52 with n-tetrabutylammonium fluoride (TBAF) leads to the formation of 2,3-dimethylene-2,3-dihydrothiophene, which is an unstable intermediate. This intermediate was captured in a Diels-Alder [4 + 2] cycloaddition reaction with methyl acrylate as the dienophile. We did not succeed in the separation of the mixture of regioisomers obtained. Hydrolysis of this mixture of esters gave the carboxylic acids 54a, b in good yield. 218 Only after conversion into the tertiary amines 34 and 35 was it possible to separate the mixture of regioisomers on a SiO2 column.
6 Oral bioavailability of dopamine receptor agonists Many dopamine receptor agonists, both of natural and synthetic origin, contain the catecholethylamine structure of dopamine embedded within them. The clinical utility of catechol and phenol-containing dopamine receptor agonists has been limited by their relatively low selectivity for presynaptic versus postsynaptic dopamine receptors, their low oral bioavailability and, consequently, their short duration of action. 181 To circumvent the problem of the low oral bioavailability of dopamine receptor ligands, synthesis of bioisosteres or prodrugs of the phenolic compounds could be useful.
Trans-9-Hydroxy-4-(2-phenylethyl)-2,3,4a,5,6,10b-hexahydro-4Hnaphth[1,2b][1,4]oxazine (27b). 61 mmol) in 30 mL of dichloromethane, under an atmosphere of nitrogen. The reaction was initially stirred for 1 h at this temperature, which was then allowed to rise to RT after which the reaction was stirred a further 3 h. The reaction mixture was then poured into water, made alkaline by the addition of a solution of NaHCO3. The separated organic layer was washed with brine, dried over Na2SO4, filtered and the solvent was removed under reduced pressure.
New, centrally acting dopaminergic agents with an improved oral bioavailability