| Abstract
| - A series of 3-spirocyclopropane-tetrahydropyrid-4-ones has been synthesized by the methodconsisting of nitrone cycloaddition to bicyclopropylidene and thermal rearrangement of the adducts.Regioisomeric 5-spirocyclopropanetetrahydropyrid-4-ones and 5-spirocyclopropanedihydropyrid-4-ones were instead obtained by cycloaddition of nitrones and nitrile oxides, respectively, tomethylenespiropentane, followed by thermal rearrangement. Methylenedispiro[2.0.2.1]heptane gave,in turn, 5,6-bis(spirocyclopropane)dihydropyrid-4-ones. The new compounds were prepared as simpleaza analogues of the cytotoxic natural products illudins and ptaquiloside in order to study theiractivity in cleaving a DNA plasmid. The activities shown by several of the compounds are moderate,but from a comparative qualitative analysis of the results a useful structure−activity relationshipfor this new class of compounds could be derived.
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