The Resolution and Absolute Configuration by X-Ray Crystallography of the Isomeric Octopamines and Synephrines
Racemates of the naturally occuring biogenic amines, o-, m-, and p-octopamine and p-synephrine, have been resolved by the preparation of suitable diastereomeric salts with antipodes of appropriate organic acids.The circular dichroism (c.d.) curves of (-)-m-octopamine hydrochloride and (-)-m-synephrine hydrochloride were superimposable and of opposite sign to those of the corresponding (-)-p-derivatives.X-ray crystallography of the (-)-3-bromocamphor-8-sulphonate salt of (-)-p-synephrine confirmed (for the first time by direct means in this series of compounds) that the absolute configuration of (-)-p-synephrine is R.It is concluded from the c.d. data that the absolute configuration of (-)-p-octopamine is also R.
Midgley, John M.,Thonoor, Mohan C.,Drake, Alex F.,Williams, Clyde M.,Koziol, Anna E.,Palenik, Gus J.
p. 963 - 970
(2007/10/02)
On the interactions of catecholamines with N-methylnicotinamide cation: A UV spectral study
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Soccorsi,Cignitti
p. 307 - 308
(2007/10/02)
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