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All Journal FIKkeS Jurnal Matematika & Sains The Journal of Pure and Applied Chemistry Research Jurnal Sains Teh dan Kina Molekul: Jurnal Ilmiah Kimia
Didin Mujahidin
Kelompok Keahlian Kimia Bahan Alam, Program Studi Kimia, Fakultas Matematika dan Ilmu Pengetahuan Alam, Institut Teknologi Bandung
Agriculture, Biological Sciences & Forestry Chemical Engineering, Chemistry & Bioengineering Chemistry Computer Science & IT Environmental Science Health Professions Industrial & Manufacturing Engineering Materials Science & Nanotechnology Mathematics Mechanical Engineering Medicine & Pharmacology

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Journal : Jurnal Sains Teh dan Kina

 1 
Synthesis of quinine N-oxide and an NMR tutorial in its structure determination Aisyah Aisyah; Nila Berghuis Tamaela; Joko Santoso; Yana Maolana Syah; Didin Mujahidin
Jurnal Penelitian Teh dan Kina Vol 17 No 1 (2014)
Publisher : Research Institute for Tea and Cinchona

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.22302/pptk.jur.jptk.v17i1.45

Abstract

Cinchona alkaloids are one of abundant natural chiral pool for organocatalysts. The application of an N-oxide group containing molecule in asymmetric reaction is currently wide developed. The structure of quinine consist two amine groups that could be oxidized to the N-oxide groups at N-1’ of quinoline and at N-1 of quinuclidine moieties. The oxidation reaction took place selectively at quinuclidine moiety by controlling the concentration of oxidizing agents. In this study we showed that N-1-oxide quinine could be occurred chemo­selectively by using a low concentration of ozone thana palladium catalyzed oxidation. The structure of products N1-oxide quinine was elucidated by spectroscopy data including 1H-NMR, 13C-NMR, 2D-NMR, infra-red and mass spectrometry. The developed method is a chemoselectively and eco-friendly method for synthesis N1-oxide quinine.
Synthesis of 1-azabicyclo[3.2.2]nonane from cinchonidine Didin Mujahidin; Hans Martin Rudolf Hoffman
Jurnal Penelitian Teh dan Kina Vol 16 No 2 (2013)
Publisher : Research Institute for Tea and Cinchona

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.22302/pptk.jur.jptk.v16i2.89

Abstract

The 1-azabicyclo[3.2.2]nonane is a potent building block which have important bio­logicaly activities including for Alzheimer and ashmatic treatment. The skeleton can be accessed by rearrangement of quinuclidine ring in Cinchona alkaloids. The rearrange­ment established three chiral center at C-2, C-3, and C-6. The rearrangement of qui­nuclidine moiety to azabicyclic[3.2.2]nonana system of mesylated cinchonidine took place by hydrolysis in a mixture of acetone–water (1:1) with 47% yields. The structure determination of the product and its absolute configuration of chiral centers were esta­blished by using spectroscopy data including, 1H NMR, 13C NMR, 1D NOE and HR-MS.
Co-Authors Aisyah Aisyah Anita Alni Euis Holisotan Hakim Hans Martin Rudolf Hoffman Joko Santoso Lia Dewi Juliawati Nila Berghuis Tamaela Shinta Ellisya Fauzia Soerya Dewi Marliyana Yana M Syah Yana Maolana Syah YAYA RUKAYADI