The primary purpose of this research project is to complete efficient total syntheses of the antitumor agents actinobolin and bactobolin from a common bicyclic lactone intermediate. This research should also make available various unnatural analogs of these natural products for antitumor testing by the National Cancer Institute. In addition, the scope, utility and applications of the intramolecular [4+2]-cycloaddition of N-acylimines with alkenes will be explored. This methodology will be applied to synthesis of penem and carbapenem precursors, to the N-terminal Alpha-amino acid components of the nikkomycins and neopolyoxins, and to polyoxamic acid, an Alpha-amino acid component of the polyoxins.

National Institute of Health (NIH)
National Cancer Institute (NCI)
Research Project (R01)
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Medicinal Chemistry Study Section (MCHA)
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Pennsylvania State University
Schools of Arts and Sciences
University Park
United States
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Seo, Jae Hong; Liu, Peng; Weinreb, Steven M (2010) Evolution of a strategy for total synthesis of the marine fungal alkaloid (+/-)-communesin F. J Org Chem 75:2667-80
Liu, Peng; Seo, Jae Hong; Weinreb, Steven M (2010) Total synthesis of the polycyclic fungal metabolite (+/-)-communesin F. Angew Chem Int Ed Engl 49:2000-3
Li, Puhui; Majireck, Max M; Korboukh, Ilia et al. (2008) A mild, efficient method for the oxidation of alpha-diazo-beta-hydroxyesters to alpha-diazo-beta-ketoesters. Tetrahedron Lett 49:3162-3164
Korboukh, Ilia; Kumar, Praveen; Weinreb, Steven M (2007) Construction of bridged and fused ring systems via intramolecular Michael reactions of vinylnitroso compounds. J Am Chem Soc 129:10342-3
Jeong, Jeannie H; Weinreb, Steven M (2006) Formal total synthesis of the cytotoxic marine ascidian alkaloid haouamine A. Org Lett 8:2309-12
Kropf, Jeffrey E; Meigh, Ivona C; Bebbington, Magnus W P et al. (2006) Studies on a total synthesis of the microbial immunosuppresive agent FR901483. J Org Chem 71:2046-55
Seo, Jae Hong; Artman 3rd, Gerald D; Weinreb, Steven M (2006) Synthetic studies on perophoramidine and the communesins: construction of the vicinal quaternary stereocenters. J Org Chem 71:8891-900
Weinreb, Steven M (2006) Studies on total synthesis of the cylindricine/fasicularin/lepadiformine family of tricyclic marine alkaloids. Chem Rev 106:2531-49
Majireck, Max M; Weinreb, Steven M (2006) A study of the scope and regioselectivity of the ruthenium-catalyzed [3 + 2]-cycloaddition of azides with internal alkynes. J Org Chem 71:8680-3
VanBrunt, Michael P; Ambenge, Reuben O; Weinreb, Steven M (2003) A mild, convenient, and inexpensive procedure for conversion of vinyl halides to alpha-haloketones. J Org Chem 68:3323-6

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