Laboratory of Synthetic Organic Chemistry
Professor
Associate Professor
(concurrent position)
Assistant Professor
Hiromichi FUJIOKA
Tomohiro MAEGAWA
Kenichi MURAI
06-6879-8225
06-6879-8226
06-6879-8227
FAX 06-6879-8229
fujioka@phs.osaka-u.ac.jp
maegawa@phs.osaka-u.ac.jp
murai@phs.osaka-u.ac.jp
Professor
Hiromichi FUJIOKA
Since the ancient times, people have been using natural plants and minerals as remedies to help curing diseases. In the course
of the 20th Century, accompanying the progress of modern science, the active principles contained in these substances has been
identified, the chemical structures of the latter have been determined, and their production by industrial organic chemistry has
become possible. We immediately entered an era of sulfa drugs and antibiotics, with a rapid improvement in the chemistry of
medicinal drugs. Now that we have stepped into the 21st Century, the genome information is being collected, and coupled with
the improvement of computers, an era where the needed drugs can be at last designed and synthesized is about to begin.
Synthetic organic chemistry is a discipline related to the creation of medicinal drugs and related compounds using methods
from organic chemistry. Our field has the objective to train exceptional synthetic organic chemists who are to be experts in the
development of new drugs, and we are involved in research with the aim to discover quality medicinal drugs. In particular, the
research is approached with interest in using organic synthesis to massively supply biologically active molecules that are
naturally present in small amounts and therefore difficult to extract. It is another important objective to perform research to
develop new organic reactions and reagents allowing the synthesis of these molecules to be completed, and to elucidate the
reaction mechanism, thereby contributing purely to the progress of organic chemistry itself. In such synthetic processes, based
on information from every field of pharmaceutical science, it will be also possible to design and synthesize useful drugs that
can outperform the ones that nature provided.
The establishment of new convenient methods for
the synthesis of peri-hydroxy polycyclic aromatic
compounds, the development of highly specific
asymmetric reactions and remote asymmetric
induction reactions that proceed via reactive cations,
the development of new reactions using ketene acetal
type compounds and asymmetric catalysts are some
results of our recent research work. By applying
these basic techniques, biologically active natural
products were synthesized in short steps by
asymmetric synthesis. In addition, while applying
these results, research is underway to synthesize
biological inhibitors that are conceived based on the
information on their receptors with the use of
computer-aided molecular design. We are also
actively involved in the development of
environment-friendly catalytic organic reactions.
Research topics
1) Development and application of novel organic reactions and reagents
2) Development of asymmetric synthetic reactions that employ reactive chemicals
3) Molecular design and synthetic chemistry for the development of medicinal drugs
4) Synthesis of antitumor antibiotics and related antitumor agents
5) Development of environment-conscious reactions
Recent publications
1) Fujioka, H. et al., Asymmetric Total Synthesis of Clavolonine. Org. Lett., 13, 2015-2017, 2011.
2) Fujioka, H. et al., The reaction of acetal-type protective groups in combination with TMSOTf and 2,2'-bipyridyl; mild and
chemoselective deprotection and direct conversion to other protective groups. Tetrahedron, 67, 2949-2960, 2011.
3) Fujioka, H. et al., Intramolecular Iodoetherification of Ene or Diene Ketals: Facile Synthesis of Spiroketals. Chem.
Commun., 47, 1060-1062, 2011.
4) Murai, K. et al., Asymmetric Bromolactonization Catalyzed by a C3-Symmetric Chiral Trisimidazoline. Angew. Chem. Int.
Ed., 49, 9174-9177, 2010.
5) Fujioka, H. et al., Remarkable effect of phosphine on the reactivity of O,P-acetal−efficient substitution reaction of
O,P-acetal. Chem. Commun., 46, 3976-3978, 2010.
6) Murai, K. et al., Facile Preparation of Oxazole-4-carboxylates and 4-Ketones from Aldehydes using
3-Oxazoline-4-carboxylates as Intermediates. Org. Lett., 12, 3456-3459, 2010.