An Alkaloid Related to Dehydrolaudanosoline

Abstract

FROM the oxidation of laudanosoline, Robinson and Sugasawa¹, and independently Schopf and Thierfelder², isolated an optically inactive quaternary ammonium salt which they showed had the structure (I) and which was named ‘dehydrolaudanosoline’. Since the oxidation proceeded so readily and so smoothly, the latter authors suggested that it might reasonably be assumed that it also occurred in the plant cell, but they were unable to cite any alkaloid which was, or could be, a derivative of (I). Later, Folkers, Koniuszy and Shavel³ ascribed to certain alkaloids of Eyrthrina species structures based on the ring system of (I); but recent work of Carmack, McKusick and Prelog⁴ has shown that other structures are more likely.