Facile and Efficient Total Synthesis
of Taspine

Bin Cheng; Sanqi Zhang; Liyong Zhu; Jie Zhang; Qiang Li; Ailin Shan; Langchong He

doi:10.1055/s-0029-1217393

PAPER

Facile and Efficient Total Synthesis of Taspine

Bin Cheng^a, Sanqi Zhang^a, Liyong Zhu^b, Jie Zhang^a, Qiang Li^a, Ailin Shan^a, Langchong He*^a
^a Research & Engineering Center for Natural Medicine, School of Medicine, Xi’an Jiaotong University, Xi’an 710061, P. R. of China
Fax: +86(29)82655451; e-Mail: helc@mail.xjtu.edu.cn;
^b College of Chemistry & Materials Science, Shannxi Normal University, Xi’an 710062, P. R. of China

Abstract

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Abstract

The facile and efficient total synthesis of taspine was achieved in 10 steps in high yield (16.5% overall) from commercially available isovanillin. Key steps in the synthesis are preparation of a symmetrical homodimer employing a classical Ullmann coupling reaction, and introduction of an allyl substituent by the Claisen rearrangement reaction. Significantly, the facile synthetic scheme proposed in this work has the characteristics of mild reaction conditions, inexpensive reagents, higher yield, and simple operation.

Key words

taspine - natural product - total synthesis - Ullmann coupling - Claisen rearrangement

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