2111-81-1Relevant academic research and scientific papers
Total Syntheses of Aspidospermidine, N-Methylaspidospermidine, N-Acetylaspidospermidine, and Aspidospermine via a Tandem Cyclization of Tryptamine-Ynamide
Yang, Lu,Huang, Siwen,Huang, Rongkang,Hou, Anbin,Zhang, Sen,Su, Hongwei,Ding, Xiaohong,Lin, Bin,Cheng, Maosheng,Liu, Yongxiang
, p. 6471 - 6476 (2021/08/23)
The total syntheses of aspidospermidine, N-methylaspidospermidine, N-acetylaspidospermidine, and aspidospermine were achieved from a common pentacyclic indoline intermediate. The common pentacyclic indoline intermediate was synthesized on a gram scale through a Stork-enamine alkylation of 1H-pyrrolo[2,3-d]carbazole derivatives, which were prepared through a Br?nsted acid-catalyzed tandem cyclization of tryptamine-ynamide. The scalable synthesis of 1H-pyrrolo[2,3-d]carbazole afforded facile access and a practical approach to the Aspidosperma indole alkaloid family.
Divergent Asymmetric Total Synthesis of (+)-Vincadifformine, (-)-Quebrachamine, (+)-Aspidospermidine, (-)-Aspidospermine, (-)-Pyrifolidine, and Related Natural Products
Wang, Nengzhong,Du, Shuo,Li, Dong,Jiang, Xuefeng
, p. 3167 - 3170 (2017/06/23)
A uniformly strategic total synthesis of Aspidosperma alkaloids (+)-vincadifformine, (-)-quebrachamine, (+)-aspidospermidine, (-)-aspidospermine, (-)-pyrifolidine, and nine others from efficiently constructed tricyclic ketone 13 is reported. Highlights of these divergent and practical syntheses include (i) stereoselective intermolecular [4 + 2] cycloaddition to establish a C-E ring with one all-carbon quaternary stereocenter (C-5) and two bridged contiguous cis-stereocenters (C-12 and C-19), (ii) a Pd/C-catalyzed hydrogenation/deprotection/amidation cascade process to assemble the D ring, and (iii) Fischer indolization to forge the A-B ring.
(-)-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.
A SYNTHETHIC ROAD TO THE FOREST OF STRYCHNOS, ASPIDOSPERMA, SCHIZOZYGANE AND EBURNAMINE ALKALOIDS BY WAY OF THE NOVEL PHOTOISOMERIZATION
Ban, Yoshio,Yoshida, Kiyoshi,Goto, Jiro,Oishi, Takeshi,Takeda, Eiko,Ishigamori
, p. 3657 - 3668 (2007/10/02)
The novel photoisomerization of 1-acylindoles accompanied by a conversion of indole to indolenine afforded 3-acylindolenines, a so far unknown reactive species, as a major product.This reaction was thorougly investigated and applied with success to the total synthesis of Strychnos, Aspidosperma, Schizozygane and Eburnamine alkaloids through a versatile intermediate 9-membered ring system,synthesized in a one pot reaction by photolysis and the simultaneous ring enlargement.
