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Communication | Special issue | Vol 66, No. 1, 2005, pp.87-90
Published online, 18th October, 2005
DOI: 10.3987/COM-05-S(K)30
A Highly Efficient Synthesis of Trispheridine through a Construction of Tetrahydrophenanthridine Based on a Microwave-assisted Thermal Electrocyclic Reaction of an Aza 6π-Electron System

Teppei Kumemura, Tominari Choshi, Junko Yukawa, Aya Hirose, Junko Nobuhiro, and Satoshi Hibino*

*Graduate School of Pharmacy and Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Fukuyama, Hiroshima 729-0292, Japan

Abstract

A highly efficient synthesis of a phenanthridine alkaloid, trispheridine (1) has been achieved in a 74% overall yield in a four-step sequence. The key step is the construction of a tetrahydrophenanthridine based on a microwave -assisted thermal electrocyclic reaction of an aza 6¿-electron system including the benzene double bond.