Studies on the synthesis of aza analogues of illudins by cycloadditions tohighly strained methylenecyclopropanes

Citation
C. Zorn et al., Studies on the synthesis of aza analogues of illudins by cycloadditions tohighly strained methylenecyclopropanes, J ORG CHEM, 64(21), 1999, pp. 7846-7855
Citations number
53
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
21
Year of publication
1999
Pages
7846 - 7855
Database
ISI
SICI code
0022-3263(19991015)64:21<7846:SOTSOA>2.0.ZU;2-8
Abstract
A series of 3-spirocyclopropane-tetrahydropyrid-4-ones has been synthesized by the method consisting of nitrone cycloaddition to bicyclopropylidene an d thermal rearrangement of the adducts. Regioisomeric 5-spirocyclopropanete trahydropyrid-4-ones and 5-spirocyclopropanedihydropyrid-4 ones were instea d obtained by cycloaddition of nitrones and nitrile oxides, respectively, t o methylenespiropentane, followed by thermal rearrangement. Methylenedispir o[2.0.2.1]heptane gave, in turn, 5,6-bis(spirocyclopropane)dihydropyrid-4 T he new compounds were prepared as simple aza analogues of the cytotoxic nat ural products illudins and ptaquiloside in order to study their activity in cleaving a DNA plasmid. The activities shown by several of the compounds a re moderate, but from a comparative qualitative analysis of the results a u seful structure-activity relationship for this new class of compounds could be derived.