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-dih ydrosanguilutine spontaneously transforms to bis[6-(5,6-dihydrosanguil utinyl)] ether, whose structure was confirmed by X-ray analysis. Treat ment of sanguilutine chloride with aqueous ammonia gave bis[6-(5,6-dih ydrosanguilutinyl)]amine. Reaction of sanguilutine chloride with potas sium cyanide yielded 6-cyanodihpdrosanguilutine; reaction of bis[6-(5, 6-dihydrosanguilutinyl)]amine with ethanol gave 6-ethoxydihydrosanguil utine. (C) 1998 Published by Elsevier Science Ltd. All rights reserved .