43015-67-4Relevant articles and documents
Synthetic Modulation of the Peripheral 2-, 3-, 9- and 12-Oxygenation Pattern of Rotenoids
Crombie, Leslie,Josephs, Jonathan L.
, p. 2591 - 2598 (2007/10/02)
Synthetic modulations of the rotenoid munduserone, in terms of the peripheral oxygenation pattern, have been carried out for structure-activity purposes.Synthesis by propargyl Claisen rearrangement was successful in cases having 2,3-dimethoxylation in ring A (as in natural Leguminous rotenoids), but failed when this electron release was not present.Attempts to catalyse an unsuccessful case led instead to an alkylidenedihydrobenzofuranone.The rotenoid lacking 2,3-dimethoxylation was made by chromanone β-ester synthesis, as was the parent rotenoid of the Boerhaavia (monocotyledonous) group.The rotenoid 12-carbonyl can be removed by reduction and dehydration, and the resulting stilbene, when catalytically hydrogenated, gives the cis-B/C-12-deoxy compound.When the reduction is effected by dissolving magnesium in methanol a separable mixture of cis- and trans-12-deoxyrotenoids is obtained.