Thermal fragmentations of tricyclo[3.2.0.0] ring systems: Applications and mechanistic studies

ORGN 654

Michael J. Williams, Holly L. Deak, and Marc L. Snapper. Department of Chemistry, Boston College, Merkert Chemistry Center, 2609 Beacon Street, Chestnut Hill, MA 02467
Medium ring systems are important scaffolds in natural products.  Hence, the development of robust and useful methodologies for the construction of these types of systems has been studied by many groups.  Our group has shown that the thermal fragmentations of functionalized anti-tricyclo[3.2.0.02,4] ring systems offer an effective and efficient method for the generation of a bicyclo[5.3.0] medium ring architecture.  Recent studies have produced a tethered syn-tricyclo[3.2.0.02,4] ring system via iron stabilized cyclobutadiene.  Both thermal fragmentation and tether cleavage have elucidated mechanistic pathways and expanded the scope of our methodology.  Current efforts focus on the application of this methodology in target oriented synthesis.