The seed of Crotalaria grahamiana R. Wight & Walk.-Arn.
contains mono- crotaline and a new alkaloid, grahamine, which is a 3?-[(-)-2- methylbutyryl]
derivative of monocrotaline. ��
Monocrotaline is not attacked at the l,2-double bond by the usual peraoid reagents but epoxidation is accomplished by trifluoroperacetic acid in excess tri-fluoroacetic
anhydride and chloroform. Under these conditions N-oxidation does not occur,
possibly because an acylammonium complex is formed.
The stereochemistry of the pyrrolizidine triol, croalbinecine, is defined as lα-hydroxymethyl-8α-
pyrrolizidine-2β,7β-diol, by means of nuclear magnetic resonance
measurements and the conversion of croalbidine into turneforcidine.
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