Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogs and their N-oxides. Potential antitumor agents

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Abstract
(-)- and (+)-trachelanthic and (-)- and (+)-viridifloric acids were synthesized and their isopropylidene derivatives were regiospecifically coupled, at C-9, with (-)-retronecine obtained by hydrolysis of monocrotaline, isolated from Crotalaria spectabilis. Hydrolysis, followed by oxidation, led to the N-oxides of indicine, intermedine, lycopsamine and the new nonnatural product, respectively. Each of these analogs was screened in the P388 lymphocytic leukemia system at the same time as indicine N-oxide, and the results were compared. Other related analogs were prepared and similarly screened, and the results compared with those from indicine N-oxide.

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