Principal Investigator Timothy Jamison
Project Website http://web.mit.edu/chemistry/jamison/Research/Synthesis/Synthesis.html
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.).
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.