Synthetic Pursuit of (+)-Precapnelladiene via Tandem 6-exo-dig cyclization/Claisen Rearrangement

By: Victoria Iannaro '15

Advising Faculty: Timo Ovaska

Synthesizing eight-membered rings has long been a challenging task. However, recent studies from the Ovaska lab have shown that tandem 6-exo-dig cyclization/Claisen rearrangement can be used for the practical preparation of a variety of cyclooctanoid systems. This sequence requires an appropriately substituted 5-hexyn-1-ol precursor, which is activated toward cyclization via an electron-withdrawing group on the triple bond. Following base-catalyzed cyclization, rearrangement occurs readily under microwave irradiation to generate the desired eight-membered ring.

This thesis explores the application of sequential 6-exo-dig cyclization/Claisen rearrangement to the synthesis of natural product and cyclooctanoid system, (+)-precapnelladiene, and in doing so, elaborates upon the scope of this unique methodology.

This honors thesis may be viewed in its entirety at Digital Commons @ Connecticut College.

Related Fields: Chemistry, Chemistry/ Biochemistry, Environmental Chemistry