125217-79-0Relevant academic research and scientific papers
A facile and efficient synthesis of (±)-tropan-2-one
Lomenzo,Enmon,Troyer,Trudell
, p. 3681 - 3690 (1995)
The facile and efficient multigram synthesis of (±)-tropan-2-one 1 was achieved in six steps (65% overall yield) from N-methyl-3-oxopyridyl hydroiodide 3.
Synthesis and evaluation of the performance of a small molecule library based on diverse tropane-related scaffolds
Lowe, Robert A.,Taylor, Dale,Chibale, Kelly,Nelson, Adam,Marsden, Stephen P.
, (2020/03/25)
A unified synthetic approach was developed that enabled the synthesis of diverse tropane-related scaffolds. The key intermediates that were exploited were cycloadducts formed by reaction between 3-hydroxy-pyridinium salts and vinyl sulfones or sulfonamides. The diverse tropane-related scaffolds were formed by addition of substituents to, cyclisation reactions of, and fusion of additional ring(s) to the key bicyclic intermediates. A set of 53 screening compounds was designed, synthesised and evaluated in order to determine the biological relevance of the scaffolds accessible using the synthetic approach. Two inhibitors of Hedgehog signalling, and four compounds with weak activity against the parasite P. falciparum, were discovered. Three of the active compounds may be considered to be indotropane or pyrrotropane pseudo natural products in which a tropane is fused with a fragment from another natural product class. It was concluded that the unified synthetic approach had yielded diverse scaffolds suitable for the design of performance-diverse screening libraries.
ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION OF CHIRAL SULPHINYLETHENES WITH 1-METHYL-3-OXIDOPYRIDINIUM AND SOME NITRONES
Takahashi, Tamiko,Fujii, Akihito,Sugita, Jun,Hagi, Toru,Kitano, Kazuyoshi,et al.
, p. 1379 - 1390 (2007/10/02)
1,3-Dipolar cycloaddition of (R)-(+)-p-tolyl vinyl sulphoxide 1 with 1-methyl-3-oxidopyridinium 6 proceeded in a diastereoselective manner to afford the exo and endo cycloadducts 11a,b and 12a in 36percent, 7percent and 29percent yield, respectively.The a
Structure of the Calystegines: New alkaloids of the nortropane family
Ducrot,Lallemand
, p. 3879 - 3882 (2007/10/02)
Three new alkaloids have been isolated from Calystegia sepium; their structures have been established from their 1H and 13C N.M.R. spectra, and confirmed by the synthesis of model compounds.
1,3-Dipolar Cycloaddition of 1-Methyl-3-oxidopyridinium and Sulfonylethenes. A Synthesis of 2-Tropanols and Monofluorinated 2-Tropanol
Takahashi, Tamiko,Hagi, Toru,Kitano, Kazuyoshi,Takeuchi, Yoshio,Koizumi, Toru
, p. 593 - 596 (2021/10/14)
2α- and 2β-Tropanols were synthesized by 1,3-dipolar cycloaddition of phenyl vinyl sulfone and 1-methyl-3-oxidopyridinium regio- and stereoselectively.The method was extended to a preparation of 6α-fluoro-2β-tropanol from 1-(benzenesulfonyl)-1-fluoroethene.
