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Semisynthesis and Biological Activity of Stemofoline Alkaloids

  作者 Baird, MC; Pyne, SG; Ung, AT; Lie, W; Sastraruji, T; Jatisatienr, A; Jatisatienr, C; Dheeranupattana, S; Lowlam, J; Boonchalermkit, S  
  选自 期刊  Journal of natural products;  卷期  2009年72-4;  页码  679-684  
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[摘要]The semisynthesis of the Stemona alkaloids (3'R)-stemofolenol (1). (3'S)-stemofolenol (2), methylstemofoline (3), and (3'S)-hydroxystemofoline (5) and the unnatural analogues (11E)-methylstemofoline (15) and 3'R-hydroxystemofoline (11) has been achieved starting from (11Z)-1',2'-didehydrostemofoline (4). This synthesis allowed, for the first time, access to diastereomerically enriched samples of 1 and 2 and the assignment of their absolute configurations at C-3'. These compounds were obtained in sufficient quantities to allow for their biological testing. In a quantitative assay as AChE inhibitors, (11Z)-1',2'-didehydrostemofoline (4) and (3'S)-hydroxystemofoline (5) were found to be the most active.

 
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