The major objective in this research is to make significant contributions to organic chemistry and medicine through chemical studies on physiologically active natural and man-made organic compounds. Organic synthesis plays the major role in all of the proposed research topics, including: 1. stereochemical assignment of acyclic compounds through organic synthesis (universal spectroscopic database creation, mycolactone, australifungin, tethered maitotoxin analogs, and others); 2. total synthesis of pinnatoxins and related natural products (pinnatoxins B and C, spirolides, gymnodimine, azaspiracid, immobilized pinnatoxins, and others); 3. covalently cross-linked Watson-Crick base pair models; 4. conformational analysis of C-and O-glycopyranosides (human blood antige, lactose, synthetic 3-O-methyl-D-mannose-containing polysaccarides (MMP), and others); 5. immobilized tetrodotoxin; 6. total synthesis of batrachotoxin, aranotin, and YW3699. We believe that the power of organic chemistry is most effectively extended by challenging these complex systems, and much of the progress of medicine critically depends upon the extension of the power of organic chemistry. It is also our specific objective to develop practical and efficient syntheses of certain natural products and their analogs, which have high physiological activity, but are not available in appreciable amounts from natural sources. These studies are again expected to stimulate progress in medicine.
| Jensen, Erik A; Allen, Benjamin D; Kishi, Yoshito et al. (2008) Conformational analysis of a covalently cross-linked Watson-Crick base pair model. Bioorg Med Chem Lett 18:5884-7 |
| Meppen, Malte; Wang, Yonghui; Cheon, Hwan-Sung et al. (2007) Synthetic 6-O-methylglucose-containing polysaccharides (sMGPs): design and synthesis. J Org Chem 72:1941-50 |
| Hsu, Margaret C; Lee, Jinhwa; Kishi, Yoshito (2007) Synthetic 3-O-methylmannose-containing polysaccharides (sMMPs): design and synthesis. J Org Chem 72:1931-40 |
| Wang, Yonghui; Ma, Jianguo; Cheon, Hwan-Sung et al. (2007) Aggregation behavior of tetraenoic fatty acids in aqueous solution. Angew Chem Int Ed Engl 46:1333-6 |
| Hao, Junliang; Matsuura, Fumiyoshi; Kishi, Yoshito et al. (2006) Stereochemistry of pteriatoxins A, B, and C. J Am Chem Soc 128:7742-3 |
| Matsuura, Fumiyoshi; Peters, Rene; Anada, Masahiro et al. (2006) Unified total synthesis of pteriatoxins and their diastereomers. J Am Chem Soc 128:7463-5 |
| Matsuura, Fumiyoshi; Hao, Junliang; Reents, Reinhard et al. (2006) Total synthesis and stereochemistry of pinnatoxins B and C. Org Lett 8:3327-30 |
| Ghosh, Indranath; Zeng, Hongbo; Kishi, Yoshito (2004) Application of chiral lanthanide shift reagents for assignment of absolute configuration of alcohols. Org Lett 6:4715-8 |
| Adams, Christopher M; Ghosh, Indranath; Kishi, Yoshito (2004) Validation of lanthanide chiral shift reagents for determination of absolute configuration: total synthesis of glisoprenin A. Org Lett 6:4723-6 |
| Ghosh, Indranath; Kishi, Yoshito; Tomoda, Hiroshi et al. (2004) Use of a chiral praseodymium shift reagent in predicting the complete stereostructure of glisoprenin A. Org Lett 6:4719-22 |
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