86227-40-9Relevant academic research and scientific papers
(-)-STREMPELIOPINE. STEREOSELECTIVE TOTAL SYNTHESIS AND THE DETERMINATION OF ABSOLUTE CONFIGURATION
Hajicek, Josef,Trojanek, Jan
, p. 1731 - 1742 (2007/10/02)
A synthesis of (+/-)-strempeliopine (II) is described, the key step of which is the stereoselective reductive rearrangement of 18-methylene-1,2-dehydroaspidospermidine (XI).The absolute configuration of the natural (-)-base II was determined as (2S,7R,20R,21R) on the basis of the synthesis from (+)-18-methylenevincadifformine (XVII) the configuration of which was derived from a comparison of circular dichroism properties of bases with a β-anilinoacrylate chromophore.The biogenesis of the alkaloids of the schizozygane type is discussed.
