Simple and Efficient Asymmetric Synthesis of Furofuran Lignans Yangambin and Caruilignan A

Naoki Mori; Hidenori Watanabe; Takeshi Kitahara

doi:10.1055/s-2006-926271

PAPER

Simple and Efficient Asymmetric Synthesis of Furofuran Lignans Yangambin and Caruilignan A

Naoki Mori^a, Hidenori Watanabe*^a, Takeshi Kitahara^a,b
^a Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan
^b Laboratory of Natural Product Chemistry, Center for Basic Research, The Kitasato Institute, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8642, Japan
Fax: +81(3)58418019; e-Mail: ashuten@mail.ecc.u-tokyo.ac.jp;

Abstract

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Abstract

A novel asymmetric dimerization of cinnamic acid derivative was achieved in high efficiency and high stereoselectivity. By using the reaction as a key step, two furofuran lignans, yangambin and caruilignan A were synthesized in optically pure form in only 5 and 6 steps, respectively.

Key words

asymmetric synthesis - oxidative dimerization - furofuran lignan - yangambin - caruilignan

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