Synthesis and Stereochemical Characterization of Hydroxy- and Epoxy-derivatives of Rotenone |
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Authors: | Tadaaki Unai Izuru Yamamoto Hong-Ming Cheng John E. Casida |
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Affiliation: | 1. Department of Agricultural Chemistry, Tokyo University of Agriculture Setagaya-ku, Tokyo, Japan;2. Division of Entomology, University of California, Berkeley, Calif U.S.A. |
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Abstract: | One to four routes of synthesis are described for 8′-hydroxyrotenone, 5′-hydroxyrotenone, two epimers of 6′,7′-dihydro-6′,7′-dihydroxyrotenone, two epimers of 6′,7′-epoxyrotenone and the four rotenolones derived from each of these compounds. The stereochemical relationships are determined, in each case, by chemical interconversion, ORD and monochromatic rotation to assess the absolute configuration of the B/C ring juncture and by IR, MS and NMR for the cis- or trans-nature of this juncture. The new compounds described are useful standards for studies on the metabolites and photodecomposition products of rotenone insecticide chemical. |
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Keywords: | acid phosphatase inhibitor soybean acid phosphatase inhibitor |
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