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Note | Regular issue | Vol 78, No. 4, 2009, pp.1047-1056
Published online, 22nd December, 2008
DOI: 10.3987/COM-08-11606
A New and Facile Synthesis of Rutaecarpine Alkaloids

Chih-Shone Lee,* Cheng-Kuo Liu, Yen-Yao Cheng, and Che-Ming Teng

*Department of Chemistry, National Sun Yat Sen University, Kaohsiung, 80424, Taiwan, R.O.C.

Abstract

Relevant rutaecarpine analogues (1a-d) have been synthesized efficiently from the ring opened β-carboline derivatives (3a-d) as key intermediates. A unique one-pot reductive-cyclization as key reaction furnished the synthesis of rutaecarpine alkaloids in excellent yields. The key intermediates (3a-d) were prepared from tryptamine following acylation, Bischler-Napieralski cyclization, benzoylation, and oxidative cleavage of the exocyclic double bond. This new synthetic approach provides a facile access to rutaecarpine analogues with potent inhibitory effect on platelet aggregation.