Abstract
The principal alkaloid of Crotalaria
goreensis Guill. et Perr. is 7β-hydroxy-1-methylene-8β-pyrrolizidine
(II),* a (+)-heliotridane derivative with the relative configuration of
heliotridine at C7 (absolute configuration 7R, 88). Of two minor alkaloids
isolated, one is the 7β-hydroxy-8α diastereoisomer (V) (absolute
configuration 7R, 8R). The other minor alkaloid is isomeric with (II) and (V)
but does not possess a 1-methylene group. The alkaloid (V) and the enantiomer
of the principal alkaloid have been synthesized by reduction of the appropriate
1-chloromethyl-7-hydroxy-1,2-dehydropyrrolizidine with zinc and sulphuric acid.
In this reduction some of the 1-methyl-1,2-dehydropyrrolizidine is formed but
the 1-methylenepyrrolizidine is the main product.
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