Stereocontrolled total synthesis of (−)-aspidophytine

S Sumi, K Matsumoto, H Tokuyama, T Fukuyama

Index: Sumi, Shinjiro; Matsumoto, Koji; Tokuyama, Hidetoshi; Fukuyama, Tohru Tetrahedron, 2003 , vol. 59, # 43 p. 8571 - 8587

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Citation Number: 62

Abstract

The enantioselective stereocontrolled total synthesis of aspidophytine is described. The key indole intermediate was prepared by radical cyclization of 2-alkenylphenylisocyanide, followed by Sonogashira-coupling with a highly functionalized terminal acetylene. The 11- membered cyclic amine, a precursor for the formation of the aspidosperma skeleton, was synthesized using nitrobenzenesulfonamide chemistry. After construction of the ...