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Communication | Special issue | Vol 74, No. 1, 2007, pp.199-203
Published online, 12th October, 2007
DOI: 10.3987/COM-07-S(W)52
Synthesis of (-)-Trolline, (-)-Crispine A and (-)-Crispine E

Takuya Kanemitsu, Yuki Yamashita, Kazuhiro Nagata, and Takashi Itoh*

*School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan

Abstract

Biologically active 1-subsutituted tetrahydroisoquinoline alkaloids, (-)-trolline, (-)-crispine A, and (-)-crispine E were synthesized using a chiral isoquinolinecarbaldehyde as a key material. The aldehyde was readily obtained from a 1-cyanoisoquinoline, and subjected to a Horner-Wadsworth-Emmons reaction. The chiral tetrahydroisoquinoline derivative thus obtained was used for the synthesis of the optically active isoquinoline alkaloids.