Functionalized bicyclo[5.3.0] decane ring systems via fragmentation of highly strained cyclopropanes: Applications in total synthesis

ORGN 670

Andrew J. Leyhane, leyhane@bc.edu, Michael J. Williams, willibjk@bc.edu, and Marc L. Snapper. Department of Chemistry, Boston College, Merkert Chemistry Center, Boston College, 2609 Beacon Street, Chestnut Hill, MA 02467
Cyclopropanation of highly strained cyclobutenes followed by thermal rearrangement provides rapid entry into bicyclo[5.3.0] decane ring systems. Rearrangement of these systems is selective and allows for application in synthesis of guaiane sesquiterpenes. Specifically our efforts towards the synthesis of galbanol, 11-hydroxypogostol, pleocarpenene, and pleocarpenone will be highlighted.

 

Total Synthesis of Complex Molecules
8:00 AM-12:00 PM, Wednesday, August 22, 2007 BCEC -- 258A, Oral

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007