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Note | Regular issue | Vol 53, No. 7, 2000, pp.1569-1572
Published online, 1st January, 1970
DOI: 10.3987/COM-00-8894
A Synthesis of Cytonin (Taiwanin A), an Antitumor Lignan

Weir-Torn Jiaang, Chih-Liang Wang, Albert Tseng, and Shui-Tein Chen*

*Institute of Biological Chemistry, Academia Sinica, Taipei, 115, Taiwan, R.O.C.

Abstract

A new procedure for the synthesis of the antitumor substance: cytonin (taiwanin A) is described. Stobbe reaction, using diethyl succinate with piperonal in a 2:1 molar ratio, produced 2E,3E-dipiperonylidenesuccinic acid. Dehydration to the anhydride, followed by reduction with DIBALH gave hydroxy acid. Subsequent cyclization of the hydroxy acid resulted in 21% total yield of cytonin.