Rot-2′-enonic acid (2), dalpanol (4), and rotenone (5) are formed during the conversion of 9-demethylmunduserone (1) into amorphigenin (6) by Amorpha fruticosa seedlings: the 4′-E-methyl of (2) becomes predominantly the 7′-methylene of (5), leading to stereochemical proposals for a formation scheme.
L. Crombie, I. Holden, G. W. Kilbee and D. A. Whiting, J. Chem. Soc., Chem. Commun., 1979, 1143 DOI: 10.1039/C39790001143
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