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Paper | Regular issue | Vol 89, No. 2, 2014, pp.437-452
Published online, 15th January, 2014
DOI: 10.3987/COM-13-12917
Synthesis of Quinolizidinone and Indolizidinone Using N-Acyliminium Ion Cyclization and a One-Pot Procedure for Preparation of Benzoquinolizidinone

Punlop Kuntiyong,* Nuanpan Piboonsrinakara, Pijitra Bunrod, Duangkamol Namborisut, Sunisa Akkarasamiyo, Poramate Songthammawat, Chitlada Hemmara, Artid Buaphan, and Boonsong Kongkathip

*Department of Chemistry, Faculty of Science, Silpakorn University, 6 Rajamanka Nai Rd, Muang Nakhon Pathom 73000, Thailand


Quinolizidinone, and indolizidinone systems were synthesized in a non-racemic form using cyclization of chiral N-acyliminium ions. The key reactive intermediates were prepared from the corresponding 2-arylethylamine or 3-butenylamine and L-glutamic acid or L-aspartic acid. The stereocenter bearing a dibenzylamino group was used for stereocontrol and resulted in diastereomeric products. A one-pot procedure for synthesis of benzoquinolizidinone was also developed. The dibenzylamino moiety was subsequently converted via Cope elimination to the corresponding cyclic enamide which is suitable as a synthetic precursor for a variety of quinolizidine alkaloids in enantiomerically pure form.