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I Wayan Muderawan, Drs., M.S., Ph.D.

Ph.D., 1998, Griffith University (Brisbane, Australia); M.S., 1989, Gadjah Mada University (Yogyakarta, Indonesia); Drs., 1984, Udayana University (Bali, Indonesia). Post Doctoral Fellow, Griffith University (Brisbane, Australia), National University of Singapore (Singapore), and Nanyang Technological University (Singapore).

Contact Information:

Office: Department of Chemistry Education
Tel : 62-362 25072

Teaching Experiences

I am a senior chemistry lecturer in the Department of Chemistry Education, Faculty of Mathematics and Sciences, Ganesha University of Education. I have some experiences in teaching of some following subjects: organic chemistry, organic chemistry lab, organic spectroscopy, introduction to quantum chemistry, and instrumental analysis.

My philosophy in teaching is there is no innovative and creative teaching without research so to be a good researcher is to be a good teacher. Moreover, beautiful and real world could be understood by learning chemistry.

I am currently pointed as coordinator for the development of international standard teacher education of mathematics and sciences in Faculty of Mathematics and Sciences, Ganesha University of Education. This opportunity could be a good experience in the development of mathematics and sciences education in Indonesia. I also work as a consultant for International Standard School in Bali.

Research Interests

Organic Synthesis

We are interested in a range of scientific challenges and technological problems in organic synthesis.  Some of them are given bellows:

Asymmetric Synthesis

Scheme 2. C-C bond formation with new chiral centre.

We are currently developing new synthetic method using allylic stannanes for new C-C bond formation and their application in asymmetric synthesis. We intend to use functional allylic organostannes which can be easily derived from allylic alcohols to create new C-C bond with carbonyl compounds. We extend the scientific spectrum from organometallic design, through simple syntheses, to catalytic investigations and mechanistic explanation. High efficiency and broad utility are our two aims.
We have successfully applied the synthetic methodology to synthesize important g-lactone compounds. More detail, see publications on Synthesis, 1998: 1640-1644; J. Chem. Soc., Perkin Trans. 2. 2000: 957-962; and Journal of Organic Chemistry, 2001, 66: 7811-7817.

High Pressure Synthesis
High pressure can be used to promote organic reactions, such as Diels-Alder reactions, allylation reactions, and other coupling reactions. We have successfully applied high pressure mediated reactions for synthesis aniline oligomers, small molecule of electrically conducting polyaniline.  Aniline oligomers can be prepared cleanly and in high yield by the high-pressure promoted SNAr reaction of aromatic amines with fluoronitrobenzenes followed by reduction of the nitro group, Scheme 1. The aligomers can absorb ultraviolet and visible spectrum, see Figure 2.

Scheme 1. Reagents and conditions:  (a) Et3N, 1.5 GPa, 30oC or 40oC; (b) H2 Pd / C.

Figure 1. 3-D structure of aniline pentamer.

Figure 2. UV-Vis spectra of aniline oligomers.

More detail, see publication on Synthesis, 2003, 16: 2511-2517.

Synthesis of Chiral Stationary Phase
Enantioseparations are currently problem in separation science because of the nature of enantiomes. The new technologies that can be potentially used to separate enantiomer are chiral chromatography, such as chiral HPLC, chiral SFC and chiral CE. We have developed new method and technology for enantioseparation by preparation of new chiral stationary phases. New ammonium functionalized cyclodextrins can be prepared in excellent yields by displacement of 6-tosyl--cyclodextrin with alkylimidazoles, pyridine or alkylamines, Scheme 1, and achieve excellent enantioseparations of dansyl amino acids presumably due to electrostatic interactions between the cationic host and anionic guest.

Scheme 1. Synthesis of single cationic CDs for chiral selectors.

Figure 1. Typical chromatographic separation data for Rac-OH-4 using MPCCD-C20 under (a) HPLC conditions: n-hexane/2-propanol (97/3, v/v), flowrate of 1 ml/min, column oven temperature 25 ◦C and (b) SFC conditions: CO2/2-propanol (97/3, v/v), total flow of 3 ml/min, back pressure of 17.0MPa and column oven temperature of 40 ◦C.

For more information about this research, see publications on Tetrahedron Letters, 2005, 46: 1747-1749; Tetrahedron Letters, 2005, 46: 7905-7907; USPTO, Provisional Application No. 60/529,112, No. PCT/SG2004/000413, Electrophoresis, 2005, 26: 3839-3848, Analytica Chimica Acta, 2006, 555: 63-67, Journal of Separation Science, 2006, 29(2): 1849-1871, Analytica Chimica Acta, 2007, 585(2): 227-233 and Journal of Chromatography A. 2008, 1182(1): 136-140.

Chiral Ionic Liquids (CILs)
Chiral ionic liquids (CILs) are organic salts having at lease one chiral centre and are liquid at low temperature (<100oC). The ionic liquids have low vapor pressure and high boiling point. Because of these natural properties, the chiral ionic liquids have many applications such as biphasic systems, catalysts, electrolytes and as alternative solvents for substitution of conventional organic solvents for many chemical reactions. This is one of the targets of green chemistry concepts.

Figure 1. Some type of organic cations of ionic liquids.

Our research in this area focuses on the following two directions: synthesis of new chiral ionic liquids and the uses of ionic liquids in organic reactions. Currently research project is on synthesis of new chiral ionic liquids from dicarboxylic acid.

Natural Products Synthesis
Organic chemistry has played a central role in pharmaceutical industry and drug discovery. We intend to explore certain medicinal area by approaches combining organic synthesis, structure-based drug design and computational chemistry. Current on-going research projects include the follows:

• Development of methodology for the synthesis of Phorbazoles, bioactive marine sponge natural products, and biological activity study of the Phorbazoles.

Figure 1. Structure of Phorbazoles.

• Transformation of Andrographolide from Andrographis paniculata Nees.

Recent Research

• Synthesis of Bromolactone for Natural Product, Basic Research, DGHE, Department of National Education, Indonesia, 2000.
• High Pressure Synthesis of Aniline Oligomers: Trimer to Hexamer, Australian Research Council (ARC), Griffith University, Brisbane Australia, 2002.
• Synthesis and Bioactivity Test of Phorbazoles and Their Derivatives, Integrated Research for Excellence (RUT), Ministry of Science and Education, Indonesia, 2002-2004.
• Isolation and Identification of Andrographolide from Andrographis paniculata Nees, Basic Science Research, Research Grant for Higher Education, Department of National Education, Indonesia, 1 Pebruary – 30 November 2002.
• Transformation of Andrographolide to Hydro- and Hydroxy Andrographolide, Basic Science Research, Research Grant for Higher Education, Department of National Education, Indonesia, 1 Pebruary – 30 November 2003.
• Development of New Chiral Ionic Liquids, NUS-NTU-ICES-ASTAR Singapore Research Grant, Singapore, 2003-2006.
• Synthesis of Chiral Ionic Liquids from Dicarboxylic Acids, Fundamental Research, DGHE, Indonesia, 2008-2009.
• Biological Activity of Phorbazoles, Fundamental Research, DGHE, Indonesia, 2009.

Publications

I have 9 national publications, 20 international publications and 1 patent application, No. PCT/SG2004/000413, USPTO, Provisional Application No. 60/529,112. International publications were published in Synthesis, Synlett, Australian Journal of Chemistry, Journal of Chemistry Society, Perkin Trans. 2, Journal of Organic Chemistry, Tetrahedron Letters, Analytica Chemica Acta, Electrophoresis, Journal of Chromatography A, and Journal of Separation Science.