Structure and transformations of the alkaloid sanguilutine

Sodium carbonate treatment of sanguilutine chloride yielded 6-hydroxy-5,6-dihydrosanguilutine. In a non-polar environment, 6-hydroxy-5,6-dihydrosanguilutine spontaneously transforms to bis[6-(5,6-dihydrosanguilutinyl)] ether, whose structure was confirmed by X-ray analysis. Treatment of sanguilutine chloride with aqueous ammonia gave bis[6-(5,6-dihydrosanguilutinyl)]amine. Reaction of sanguilutine chloride with potassium cyanide yielded 6-cyanodihpdrosanguilutine; reaction of bis[6-(5,6-dihydrosanguilutinyl)]amine with ethanol gave 6-ethoxydihydrosanguilutine. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.