Thermal dimerization of the acridone alkaloid noracronycine ( 2 ) leads to Diels-Alder adducts ( 3 ) and ( 4 ) , possessing a rearranged structure.Acronycine ( 1 is a Rutaceous pyranoacridone alkaloid which exhibits a b r o a d spectrum of antineoplastic activity.l-3It is easily converted into its 0 -d e m e t h y l derivative, noracronycine ( 2 L 4 Polymerization and rearrangement reactions of both compounds under acidic conditions have been recently extensively studied.5All t h e dimers, trimers and polymers obtained involve creation of a single carbon-carbon bond, b e t w e e n t h e positions 1 and 5 of t w o d i f f e r e n t units, sometimes w i t h simultaneous rearrangement.>Nevertheless, the 2.2-dimethylpyran ring of t h e s e compounds led us t o envisage the possibility of a different w a y of dimerization.leading to Diels-Alder derived alkaloid dimers.This type of reaction is known in t h e field of prenylated coumarins and alkaloids 6 a n d h a s been also studied in t h e case of
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Tillequin et al. (1992) studied this question.