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Communication | Special issue | Vol 72, No. 1, 2007, pp.91-94
Published online, 22nd December, 2006
DOI: 10.3987/COM-06-S(K)7
A New Method for Efficient Coupling of Indole and Epoxide Catalyzed with Yb(OTf)3, and Application to the Total Synthesis of Kurasoin B

Satoshi Tsuchiya, Toshiaki Sunazuka, Tatsuya Shirahata, Tomoyasu Hirose, Eisuke Kaji, and Satoshi Omura*

*Kitasato Institute for Life Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8642, Japan

Abstract

The Yb(OTf)3 catalyzed reaction between indole and epoxide in simple and mild condition was developed. This method is suitable for gram-scale synthesis of 3-indolelactic acid derivatives. The asymmetric synthesis of kurasoin B was achieved using chiral 3-indolelactic acid methyl ester as the starting material.