Our efforts towards the total synthesis of rutaecarpine via novel homo aza-Nazarov cyclization of cyclopropanoyl quinazolinone were not successful in providing desired mackinazolinedione due to the formation of competing, yet interesting, furyl derivative formation via a Cloke-Wilson rearrangement, and pyrrole derivative formation via a 3+2 cycloaddition of ACN, etc. Efforts towards rutaecarpine with a revised retrosynthetic approach involving imino homo aza-Nazarov afforded interesting diaza-Pummerer type product in DMSO/TfOH reflux. Finally, the later attempts of refluxing advanced imine intermediate in neat TfOH successfully afforded the desired rutaecarpine with varying isolated yields based on the temperature of the reaction. The best result thus far was realized in refluxing TfOH at 60oC overnight that afforded the 52% isolated yield of rutaecarpine. The details will be presented.

Synthesis of Rutaecarpine via novel homo aza-Nazarov cyclization of cyclopropanoyl quinazolinone

ACS Spring Meeting 2021

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