Beilstein J. Org. Chem.2019,15, 1612–1704, doi:10.3762/bjoc.15.165
failure), zolpidem (for treatment of insomnia), zolimidine (antiulcerdrug), alpidem and saripidem (anxiolytic agents) and some are under development, like GSK812397 (for the treatment of HIV), ND-09759 and Q203 (for tuberculosis) (Figure 1) [6][7][8][9][10].
The synthesis of imidazopyridines (IPs) is
protocol also provided a concise route for the synthesis of the antiulcerdrug zolimidine in 95% yield. A three-component coupling reaction (3-CCR) for the synthesis of N-fused pyridines was reported by Balijapalli and Iyer [40]. The reaction was catalyzed by CuO/CuAl2O4 and ᴅ-glucose. The reaction had
Beilstein J. Org. Chem.2016,12, 2234–2239, doi:10.3762/bjoc.12.215
rosaprostol (1), an antiulcerdrug, were efficiently synthesized from the enantiomers of 2-(dimethoxyphosphoryl)-3-hexylcyclopentanone (3) as chiral substrates. The latter were obtained by resolution of racemic 3 with (+)-(R)-1-(1-naphthyl)ethylamine. The conversion of (+)-3 into rosaprostol stereoisomer
to 64%. The remaining two stereoisomers, (−)-1b and (+)-1d, were obtained from (−)-1a and (+)-1c in 71 and 68% yield, respectively, by a two-reaction sequence, in which a Mitsunobu inversion of configuration at C-5 was the key step.
Keywords: antiulcerdrug; chiral resolution; rosaprostol
-nitrobenzoates (+)-10 and (−)-10 were isolated and fully characterized (see Supporting Information File 1 for details).
Conclusion
In summary, a new concise and efficient synthesis of the four enantiomerically pure stereoisomers of rosaprostol (1), an antiulcerdrug, was accomplished. The stereoisomers (−)-1a
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Graphical Abstract
Figure 1:
Structure of rosaprostol (1) and numbering system.