Research in the Jamison Group

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Target-Oriented Synthesis

   Natural product synthesis in the Jamison laboratory is closely linked to the development of new transformations and the elucidation of reaction mechanism. Methods developed in the group are used to gain rapid access to the core structures of targets bearing unique structural features and interesting biological activity.

   Regioselective epoxide-opening cascades, for example, have emerged as a powerful method to construct complex fused ring systems in a single step from an appropriate polyepoxide precursor. The Jamison group has completed the total synthesis of terpenoid polyether dioxepandehydrothyrsiferol utilizing an epoxide-opening cascade and similar efforts are underway to prepare marine ladder polyether natural products (e.g., gambierol, brevenal, etc.).
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   In addition, Ni-catalyzed transformations have been employed to intercept key intermediates of various polyketide natural products. Ni-catalyzed reductive macrocyclizations were used to access highly advanced intermediates in the total syntheses of amphidinolide T1 and gloeosporone, among others. Intermolecular fragment coupling methods have also been used succesfully to construct complex structures, such as a macrocyclization precursor en route to the total synthesis of terpestacin.
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Representative Publications:
  • Kleinke, A. S.; Webb, D.; Jamison, T. F. "Recent progress in the synthesis of oxepanes and medium ring ethers" Tetrahedron 2012, 68, 6999-7018. Download PDF
  • Tanuwidjaja, J.; Ng, S.-S.; Jamison, T.F. "Total Synthesis of ent-Dioxepandehydrothyrsiferol via a Bromonium-Initiated Epoxide-Opening Cascade" J. Am. Chem. Soc. 2009, 131, 12084-12085. Download PDF
  • Van Dyke, A. R.; Jamison, T. F. "Functionalized Templates for the ConvergentAssembly of Polyethers: Synthesis of HIJK Rings of Gymnocin A" Angew. Chem., Int. Ed. 2009, 48, 4430-4432. Download PDF
  • Trenkle, J. D.; Jamison, T. F. "Macrocyclization by Nickel-Catalyzed, Ester-Promoted, Epoxide-Alkyne Reductive Coupling: Total Synthesis of (-)-Gloeosporone" Angew. Chem., Int. Ed. 2009, 48, 5366-5368. Download PDF
  • Colby, E. A.; O'Brien, K. C.; Jamison, T. F. "Total Syntheses of Amphidinolide T1 and T4 via Catalytic, Stereoselective Reductive Macrocyclizations" J. Am. Chem. Soc. 2005, 127, 4297-4307. Download PDF
  • Chan, J.; Jamison, T. F. "Enantioselective Synthesis of (−)-Terpestacin and Structural Revision of Siccanol Using Catalytic Stereoselective Fragment Couplings and Macrocyclizations" J. Am. Chem. Soc. 2004, 126, 10682-10691. Download PDF