79808-94-9Relevant academic research and scientific papers
STEREOSPECIFIC TOTAL SYNTHESIS OF (+/-)-STREMPELIOPINE
Hajicek, Josef,Trojanek, Jan
, p. 2927 - 2928 (1981)
The 18-methylene-1,2-dehydroaspidospermidine (III) was stereospecifically transformed into the schizozygane alkaloid strempeliopine (II) in 16,6 percent overall yield.
Application of cross-conjugated heteroaromatic betaines to the synthesis of the schizozygane alkaloid (±)-strempeliopine
Bobeck, Drew R.,Hyoung, Ik Lee,Flick, Andrew C.,Padwa, Albert
experimental part, p. 7389 - 7402 (2010/02/17)
(Chemical Equation Presented) An efficient stereocontrolled route to the isoschizozygane alkaloid core has been developed utilizing an intramolecular 1,4-dipolar cycloaddition of a cross-conjugated heteroaromatic betaine. The resulting cycloadduct undergo
(-)-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.
