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Synthesis 2006(3): 400-404  
DOI: 10.1055/s-2006-926271
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Naoki Moria, Hidenori Watanabe*a, Takeshi Kitaharaa,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;
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Publication History

Received 18 September 2005
Publication Date:
11 January 2006 (online)

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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