Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
10587593 | Bioorganic & Medicinal Chemistry Letters | 2013 | 7 Pages |
Abstract
Unexpected sequential E-ring dihalogenation of podophyllotoxin analogues is reported. It demonstrated that a chlorine/bromine atom was prior introduced at the C2â² position of podophyllotoxin, and the corresponding free rotation of E-ring around the C1-C1â² bond of 2â²-chloro or 2â²-bromopodophyllotoxin was restricted. When 2â²-chloro or 2â²-bromopodophyllotoxin reacted with N-chlorosuccinimide (NCS), the chlorine atom was regioselectively introduced at their C6â² position on the E-ring. Whereas 2â²-chloro or 2â²-bromopodophyllotoxin reacted with NBS, the bromine atom was regioselectively introduced at their C5 position on the B-ring. When 2â²-chloropodophyllotoxin reacted with different carboxylic acids in the presence of BF3·Et2O, the steric effect of its E-ring for stereoselective synthesis of 4β-acyloxy-2â²-chloropodophyllotoxin derivatives was observed. The insecticidal activity of 2â²(2â²,6â²)-(di)halogen-substituted podophyllotoxin derivatives were evaluated with Mythimna separata Walker.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Zhiping Che, Xiang Yu, Lingling Fan, Hui Xu,