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Communication | Regular issue | Vol 12, No. 12, 1979, pp.1523-1528
Published online, 1st January, 1970
DOI: 10.3987/R-1979-12-1523
Stereoselective Total Synthesis of Optically Active trans- and cis-Burseran. Determination of the Stereochemistry of Natural Antitumor Burseran

Kiyoshi Tomioka and Kenji Koga*

*Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan

Abstract

Optically pure trans- and cis-burseran were synthesized stereoselectively from (R)-(+)-β-piperonyl-γ-butyrolactone (2). Both compounds gave satisfactory 13C NMR spectra. By comparing their behavior on gas chromatography, the naturally occurring burseran characterized as an antitumor agent was determined to be the trans-isomer.