Michio Kurosu Assistant Professor of Chemistry Ph.D., Osaka University, 1995 Postdoctoral Fellow, Harvard University, 1995-1999

Department of Chemistry  The Florida State University Tallahassee, Florida 32306-4390 TEL: (850)644-2333 FAX: (850)644-8281 E-MAIL: kurosu@chem.fsu.edu

Synthetic Organic Chemistry

1. The development of practical and widely applicable synthetic methods and their applications to the total synthesis of complex natural products:  Our concept along these lines is the investigation of stable (asymmetric) catalysts and biochemicals with activities that are predictable and controllable, and the development of environmentally acceptable synthetic processes that are also economically acceptable.  We are focusing on the following topics:

          • efficient carbon-carbon forming reactions in aqueous media
          • mimicking of enzymatic reactions
                    oxidation and reductions
                    selective cleavage of a and b-glycosides
                    mild amide bond cleavage reactions
          • efficient glycosidation methods
 

2. The total synthesis of complex natural products: We are especially interested in natural products which have been synthetically and biosynthetically undeveloped: verutram alkaloids (germine), unusual steroidal fungus metabolites (citeohybridone C), diketopiperazine natural products (aranotin), and ladder polyethers (ciguatoxin).  Many of them are rare substances, available in minute quantities from natural sources, and all are of biological significance.  For the construction of stereogenic centers, the strategy demands highly enantioselective reagents and/or catalysts.  Our research in this field involves the development of new synthetic methods and strategies, and reagents.  Our main goal is to establish general strategies for various classes of important carbocyclic and heterocyclic natural products.  In addition, we expect to develop fundamental organic reactions with a detailed understanding of their reaction mechanisms along the way.

Bioorganic Chemistry

In the bioorganic area, we are currently interested in:

1. Glycoconjugates, represented by gangliosides GQ_1b and GT₃, which play critical roles in numerous biological phenomena, such as cell-cell adhesion, malignancy, and cell growth regulation.  It is therefore of prime interest to systematically synthesize these glycoconjugates in order to evaluate the biological function.

2. Specific apoptosis inducers, such as apoptolidin, which may be useful as anti-cancer agents.  Work in this area is also concerned with the design and synthesis of artificial biologically active molecules.  In order to investigate the understanding of mechanism of the biological activity at the molecular level, a number of collaborative studies will be envisioned.

"Total Synthesis of (±)-Batrachotoxinin A,"  Kurosu, M.; Marcin, L. R.; Grinsteiner, T. J.; Kishi, Y. J. Am. Chem. Soc. 1998, 120, 6627.

"A Useful Modification of the Garst-Spencer Furan Annulation: An Improved Synthesis of 3,4-Substituted Furans,"  Kurosu, M.; Marcin, L. R.; Kishi, Y.  Tetrahedron Lett. 1998, 39, 8929.

"A Novel Example for Optical Resolution of Racemic Ketones Originating from Batrachotoxin Synthesis,"  Kurosu, M.; Kishi, Y.  J. Org. Chem. 1998, 63, 6100.

"Reaction of Methylcerium Reagent with Tertiary Amides: Synthesis of Saturated and Unsaturated Ketones from Tertiary Amides,"  Kurosu, M.; Kishi, Y.  Tetrahedron Lett. 1998, 39, 4793.

"A Total Synthesis of Arenastatin A, an Extremely Potent Cytotoxic Depsipeptide from the Okinawan Marine Sponge Dysidea arenaria,  Kobayashi, M.; Kurosu, M.; Wang, W.; Kitagawa, I.  Chem. Pharm. Bull. 1994, 42, 2394.

"Sphingolipids and Glycerolipids IV. Syntheses and Ionophoretic Activities of Soya-cerebroside II, a Calcium Ionophoretic Sphingoglycolipid Isolated from Soybean,"  Shibuya, H.; Kurosu, M.; Minagawa, K.; Katayama, S.; Kitagawa, I.  Chem. Pharm. Bull. 1993, 41, 1993.