(Synthetic Organic Chemistry)
(Synthetic Organic Chemistry)
B.S. Hokkaido University (1991)
M.S. Hokkaido University (1993)
Ph.D. Nagoya University (1996)
Research Fellow of the Japan Society for the Promotion of Science at Nagoya University (1996~1997)
Research Fellow of the Japan Society for the Promotion of Science at The Scripps Research Institute (1997~1998)
Research Associate at Tokyo University of Science (1998~2003)
Assistant Processor at Waseda University (2003~ )
keywords
organic synthesis, total synthesis, bioactive compound,
ketene N,O-acetal, remote stereocontrol
Room 65-206
3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan
Tel: +81-3-5286-8127
Fax: 81-3-3200-3203
E-mail:seijiro@waseda.jp
Research Interests
Chemistry is a field of making molecule as we like, however, construction of a molecule such as a natural product is still difficult problem. The power of construction of molecules is important to produce a new field of science. So I study chemistry to be "a master of creation and treatment of molecules" and study on synthetic organic chemistry including establishment of new methodologies and total syntheses of bioactive natural products.
It is neccesary to realize these subjects that discovery of efficient touts to construct the target molecules. Especially, in the case of the route to the complex molecule, there are steps which have been never realized so far and /or have been never overcome by known methodologies. Such a case is a chance to create and discover new chemistry. So we solute these problems by establish our original methods.
Additionally, in the studies toward of the total synthesis of a complex molecule, there are intermediates which has novel alignment of functional groups. Such cases are also chances to find new chemistry. We are interested in such alignment to disclose the potent reactivity of the functional groups.
Herein we present a few examples. At first, in the total synthesis of madindoline A, an inhibitor of IL-6 activity, we established a novel methodology to construct a quaternary carbon, a novel hydroamination to couple an sterically hindered aldehyde and an acid-sensitive amine, and a novel methodology to construct a cyclopentendione. Secondary, we were interested in an by-product in the reaction to afford the chiral quaternary carbon and we establish a rearrangement reaction of ketene-N,O-acetals. At third, by observation of a by-product of the rearrangement reaction, we discovered a novel remote stereoinduction of silylketene-N,O-acetals. Application of this reaction to the bioactive polyketids is in progress.
Additionally, to construct highly oxygenated compounds, especially compounds bearing tertiary alcohols, we established a novel stereoselective aldol reaction using a lactate derivative bearing a chiral auxiliary. This reaction was applied to the concise and highly stereoselective synthesis of citreoviral bearing
As shown in these examples, we study total syntheses in accompany with establishment of new methodologies. The total synthesis of a bioactive product supplies the compound in sufficient amount and makes possible to investigate the bioaction of the compound and to make derivatives to be new drugs.
Recently, we study on total syntheses of bioactive natural products, the remote stereoinduction reaction, and its application to polyketids. We are also interested in the bioaction and physical property of tte compounds and production of new drugs.
Now we are evolving "Chemistry Oriented Target Molecules".
Representative Publications
1."Stereoselective Construction of a Quaternary carbon Substituted with Multifunctional Groups: Application to the Concise Synthesis of (+)-Ethosuximide", Tetrahedron Letters, 44(52), 9303-9305 (2003).
2."1,3-Rearrangement of Ketene N,O-acetals", Tetrahedron Letters, 44(18), 3713-3716 (2003).
3."Stereocontrolled Preparation of 1,2-diol with Quaternary Chiral Center", Tetrahedron Letters, 43(45), 8021-8023 (2002).
4."Total Synthesis of Madindoline A", J. Synth. Org. Chem., Jpn, 59(11), 1103-1108 (2001)
5." Mirror Image Synthesis of Left Ends of Ciguatoxin and Gambiertoxin 4B", J. Org. Chem. 64(1), 37-48 (1999).
6."Reductive Decomplexation of Biscobaltcarbonyl Acetylenes into Olefins", Tetrahedron Letters, 39, 2609-2612 (1998).
7."1,4-anti Induction in C-Glycosilation of Pentose Glycals", Tetrahedron Letters, 39, 1917-1920, (1998).
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