23360-86-3Relevant academic research and scientific papers
Highly efficient synthesis of tricyclic amines by a cyclization/ cycloaddition cascade: Total syntheses of aspidospermine, aspidospermidine, and quebrachamine
Coldham, Iain,Burrell, Adam J. M.,White, Laura E.,Adams, Harry,Oram, Niall
, p. 6159 - 6162 (2007)
(Chemical Equation Presented) Three in one: Three new rings can be made in one pot with complete control of the regio- and stereochemistry by a tandem cyclization/cycloaddition cascade reaction. Treatment of a chloroaldehyde with an amine gives a cyclic azomethine ylide that undergoes intramolecular cycloaddition onto a tethered alkene. The method was applied to the shortest known synthesis of aspidospermine (see scheme).
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 total syntheses of (-)-aspidospermine and (+)-spegazzinine
Lajiness, James P.,Jiang, Wanlong,Boger, Dale L.
, p. 2078 - 2081 (2012/06/18)
Divergent total syntheses of (+)-spegazzinine (1) and (-)-aspidospermine (2) and their extensions to the synthesis of C19-epi-aspidospermine and C3-epi-spegazzinine are detailed, confirming the relative stereochemistry and establishing the absolute configuration of (+)-spegazzinine. A powerful intramolecular [4 + 2]/[3 + 2] cycloaddition cascade of a 1,3,4-oxadiazole provided the pentacyclic skeleton and all the requisite stereochemistry of the natural products in a single reaction that forms three rings, four C-C bonds, and five stereocenters.
