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Report | Regular issue | Vol 14, No. 11, 1980, pp.1767-1770
Published online, 1st January, 1970
DOI: 10.3987/R-1980-11-1767
Synthesis and Structural Assignment of Naturally Occuring 3-Benzyl-6-benzylidene-2,5-piperazinedione

Chung-gi Shin,* Haruo Kato, Yasuchika Yonezawa, Masato Hayakawa, and Juji Yoshimura

*Departmnet of Applied Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan

Abstract

Four possible stereoisomers of 3-benzyl-6-benzylidene-2,5-piperazinedione were synthesized, and the configuration of the natural product isolated from Streptomyces noursei was determined to be (3R, 6Z). It was found that the sign of the optical rotations and the Cotton effect are reversed only by the difference of the (E)- or (Z)-geometry.