Synthetic applications of optically active cyanohydrins. Enantioselective syntheses of the hydroxyamides tembamide and aegeline, the cardiac drug denopamine, and some analogues of the bronchodilator salbutamol |
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Authors: | Roger F. C. Brown Andrew C. Donohue W. Roy Jackson Tom D. McCarthy |
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Affiliation: | Department of Chemistry, Monash University, Clayton, Victoria, Australia 3168. |
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Abstract: | The natural hydroxyamides, (−)-tembamide and (−)-aegeline, and the cardiac drug (−) -denopamine have been prepared in homochiral form in good overall yield (>65%) from para - methoxy or para-allyloxybenzaldehyde by synthetic sequences involving entantioselective hydrocyanation of the aldehydes. Similar chemistry has been used to prepare analogues of the bronchodilator (−)-salbutamol both in high yield and with good enantiomeric excess. |
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