Semisynthesis and acetylcholinesterase inhibitory activity of stemofoline alkaloids and analogues

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Journal Article
Journal of Natural Products, 2010, 73 (5), pp. 935 - 941
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Semisynthesis of the known Stemona alkaloids oxystemofoline (7) and methoxystemofoline (8) has been achieved starting from (11Z)-1′,2′- didehydrostemofoline (6), which confirmed their structures and absolute configurations. The synthesis of (1′R)-hydroxystemofoline (9) helped establish this compound as a natural product from Stemona aphylla. (1′S)-Hydroxystemofoline (10) and a number of related analogues were also prepared. In a TLC bioautographic assay, 9 was found to be the most active acetylcholinesterase inhibitor, but it was not as active as galanthamine. © 2010 The American Chemical Society and American Society of Pharmacognosy.
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