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Communication | Special issue | Vol 90, No. 1, 2015, pp.150-156
Published online, 24th July, 2014
DOI: 10.3987/COM-14-S(K)46
Total Syntheses of Zwitterionic Indole Alkaloids, Flavocarpine and Dihydrovincarpine, by Extended Method for Substituted Pyridine Synthesis through Azaelectrocyclization

Yoshikatsu Hirose, Hiroshi Tsuchikawa, Toyoharu Kobayashi,* and Shigeo Katsumura*

*School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan

Abstract

The total syntheses of flavocarpine (1) and dihydrovincarpine (2) have been accomplished through the common intermediate, 2,4,5-trisubstituted pyridine compound 3 which was prepared by the accelerated 6π-azaelectrocyclization of 4-alkoxycarbonylazatriene 4 followed by aromatization of the resulting dihydropyridine derivative.