Agricultural and Biological Chemistry
Online ISSN : 1881-1280
Print ISSN : 0002-1369
ISSN-L : 0002-1369
Synthesis and Stereochemical Characterization of Hydroxy-and Epoxy-derivatives of Rotenone
Tadaaki UNAIIzuru YAMAMOTOHong-Ming CHENGJohn E. CASIDA
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1973 年 37 巻 2 号 p. 387-401

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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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