Pyrrolo-[2,1-j]quinolone is a commonly found core structure in the family of tricyclic marine alkaloids such as Lepadiformine and Cylindricine. These alkaloids have been reported to have cytotoxicity against cancer cells, antiarrhythmic properties and other cardiovascular effects. The challenging Pyrrolo-[2,1-j]quinolone core structure have been synthesized in only two steps starting from 6-methoxytetrahydroquinoline, using electrophilic cyclization as a key step. These reactions require simple starting materials and milder reaction conditions. In addition, we have also demonstrated that the Iodine moiety, which could easily be introduced in the final step, is very useful for further functionalization by employing various palladium catalyzed cross coupling reactions.                 

Synthesis of Pyrrolo-[2,1-j]quinolone framework via intramolecular ipso-Iodocyclization

244th National Meeting (2012)

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