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Member Information
Amos B. Smith III, PhD
Rhodes-Thompson Professor of Chemistry, Department of Chemistry
Member, Department of Chemistry and the Monell Chemical Senses Center
University of Pennsylvania
Visiting Director, Kitasato Institute, Tokyo , Japan
Office Phone: 215-898-4860
Office Fax: 215-898-5129
Email: smithab@sas.upenn.edu
Website(s):
Education: PhD 1972, The Rockefeller University
Keywords: organic synthesis, bioorganic chemistry, materials science
Research and/or Clinical Interests:
Our research falls into three areas: Organic Synthesis, Bioorganic Chemistry amd Materials Science.
Summary:
At present, we are engaged in the total synthesis of a number of architecturally novel antibiotic, antifungal, and antitumor agents. These include the spongistatins, breynins A and B, calyculin A, cylindrocyclophane A, discodermolide, the macrolactins, the phorboxazoles, penitrem D, and tedanolide. As you are aware we try to incorporate new photo and/or thermal arrangement chemistry in the various synthetic strategies. In addition, I am involved in collaborative programs in bio-organic and materials chemistry. The first project, in collaboration with Professor Ralph Hirschmann, concerns the design and synthesis of non-peptide peptidomimetics; the second, in collaboration with Professor Paul Heiney, involves the construction of novel materials including discotic liquid crystals and derivatives of C60 and the higher fullerenes. A third, long-standing interest of my laboratory concerns the isolation of natural products. Here, I have a very exciting collaboration with Professor Satoshi Omura, President of the Kitasato Institute in Tokyo , Japan .
Representative Publications:
A. B. Smith, III, S. M. Condon, and J. A. McCauley, "Immunosuppressants as Synthetic Targets: Unified Construction Strategies," Acc. of Chem. Res. , 31 , 35-46 (1998).
A. B. Smith, III, G. Ott, "Total Synthesis of (-)-Macrolactin A, (+)-Macrolactin E and (-)-Macrolactinic Acid: An Exercise in Stille Cross-Coupling Chemistry," J. Am. Chem. Soc ., 120 , 3935-3948 (1998).
A. Khong, H. A. Jiménez-Váquez, M. Saunders, R. J. Cross, J. Laskin, T. Peres, C. Lifshitz, R. Strongin and A. B. Smith, III, "An NMR Study of He2 Inside C70," J. Am. Chem. Soc ., 120 , 6380-6383 (1998).
A. B. Smith, III, G. K. Friestad, J. J.-W. Duan, J. Barbosa, K. G. Hull, M. Iwashima, Y. Qiu, E. Bertounesque, P. G. Spoors and B. A. Salvatore, "Total Synthesis of (+)-Calyculin A and (-)-Calyculin B," J. Org. Chem ., 63 , 7596-7597 (1998).
A. B. Smith, III, D. A. Favor, P. A. Sprengeler, M. C. Guzman, P. J. Carroll, G. T. Furst and R. F. Hirschmann, "Molecular Modeling, Synthesis, and X-Ray Crystal Structures of N-Methylated 3,5-Linked Pyrrolin-4-ones Toward the Creation of a Privileged Nonpeptide Scaffold," Bioorg. Med. Chem., 7, 9-22 (1999).
