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Communication | Regular issue | Vol 24, No. 4, 1986, pp.913-917
Published online, 1st January, 1970
DOI: 10.3987/R-1986-04-0913
Studies on the Chemical Transformation of Rotenoids. I. Ring Transformation of (-)-(6aS,12aS,2R)-Rotenone into Benzopyrano[3,4-c]pyrazoles

Shin-ichi Nagai, Teppei Akiyama, Taisei Ueda, Noriichi Oda, and Jinsaku Sakakibara*

*Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan

Abstract

Rotenone (1) underwent the ring transformation into 3-substituted 1-(2-methylethenyl-4-hydroxy-2,3-dihydrobenzofuran-5-yl)-7,8-dimethoxy-1,9b,2,3,3a,4-hexahydro-[1]benzopyrano[3,4-c]pyrazol-1-enes (4a-e) when treated with hydrazines in the strong basic medium. The stereochemistry of the products was established by 1H-NMR spectra confirming the cis B/C fusion.