A general strategy for synthesis of phenylethanoid glycosides (PhG) including echinacoside 1, acteoside 2, calceolarioside-A 3, and calceolarioside-B 4 is reported. The strategy features the application of low substrate concentration glycosylation and N-formylmorpholine modulated glycosylation methods for construction of 1,2-trans alpha- and beta-glycosidic bonds. The reported strategy does not invoke the use of participatory acyl protecting function, which is incompatible with the ester function present in target PhG compounds. Preliminary study of anti-proliferation property of the PhG compounds 1 to 4 was performed; the acteoside 2 exhibited the best inhibition on the prostatic cancer cell proliferation.
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Organic & Biomolecular Chemistry
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