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4β-Azido-4-demethyl-4’-O-demethyl-epipodophyllotoxin reacted with phenyliodonium diacetate in MeOH at room temperature to synthesize a novel podophyllotoxin derivative containing a cyclohexadienone group with the original configurations of C2 and C4,which are required for the antitumor activities.The component and structure of the pro-duct were confirmed using elemental analysis,high-resolution mass spectrum,1H and 13C NMR spectra,and infrared spectrum.Furthermore,the fragmentation routes of the product were fully assigned with electron-impact time-of-flight mass spectrometry(EI-TOF MS),which can also be used for the structural elucidation based on the molecular ion at m/z 455(16%)and three novel characteristic fragment ions at m/z 183(37%),425(7%),and 199(5%).The cyclohexadienone product is sensitive to acidic media.When it is treated with a trace of acid,another novel derivative containing an orthoquinone moiety is formed,which links with the metabolism of the cancer inhibitors.
4β-Azido-4-demethyl-4’-O-demethyl-epipodophyllotoxin reacted with phenyliodonium diacetate in MeOH at room temperature to synthesize a novel podophyllotoxin derivative containing a cyclohexadienone group with the original configurations of C2 and C4, which are required for the antitumor activities. Component and structure of the pro-duct were confirmed using elemental analysis, high-resolution mass spectrum, 1H and 13C NMR spectra, and infrared spectrum. Stillrther, the fragmentation routes of the product were fully assigned with electron-impact time- of-flight mass spectrometry (EI-TOF MS), which can also be used for the structural elucidation based on the molecular ion at m / z 455 (16%) and three novel characteristic fragment ions at m / z 183 , 425 (7%), and 199 (5%). The cyclohexadienone product is sensitive to acidic media. Another novel derivative containing an orthoquinone moiety is formed, which links with the metabolism of the cancer inhibitors.