New types of norcantharimide analogues were prepared by three methods: epoxidation, photooxidation, and bromination. Epoxidation of deoxynorcantharimide with m-chloroperoxybenzoic acid gave an isomeric mixture. The selective formation of the synisomers was attributed to dipole-dipole interactions between the peracid and imide moiety. Photooxidation of deoxynorcanthamide gave syn-and anti-hydroperoxide analogues through ene addition of singlet oxygen; the anti-hydroperoxide was the major product in this case, as a result of the steric effect of the imide ring. Bromination of deoxynorcantharimide and subsequent transformations gave a pyrrolidine and the phthalimide core structure.
A new and appropriate synthesis for hexahydro-1H-isoindole-1,3(2H)-dione derivatives has been developed starting from 3-sulfolene. The epoxidation of 2-ethyl/phenyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3-(2H)-dione and then the opening of the epoxide with nucleophiles gave hexahydro-1H-isoindole-1,3(2H)-dione derivatives. Amino and triazole derivatives of hexahydro-1H-isoindole-1,3(2H)-dione were synthesized from the formed product by the opening reaction of the epoxide with sodium azide. Hydroxyl analogues were obtained from cis-hydroxylation of 2-ethyl/phenyl-3a,4,7,7atetrahydro-1H-isoindole-1,3-(2H)-dione. The hydroxyl groups were converted to acetate.
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