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

Roger F.C. Brown, Andrew C. Donohue, W. Roy Jackson, Tom D. McCarthy

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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.

Original languageEnglish
Pages (from-to)13739-13752
Number of pages14
JournalTetrahedron
Volume50
Issue number48
DOIs
Publication statusPublished - 1 Jan 1994

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