Total synthesis of pleocarpenene and pleocarpenone

ORGN 452

Michael J. Williams, willibjk@bc.edu1, Holly L. Deak2, and Marc L. Snapper1. (1) Department of Chemistry, Boston College, Merkert Chemistry Center, 2609 Beacon Street, Chestnut Hill, MA 02467, (2) Amgen, Inc, 1 Kendall Square, Bldg 1000, Cambridge, MA 02139
Medium ring systems are important scaffolds in natural products; hence, the development of robust and useful methodologies for their construction is imperative. Intramolecular cycloadditions of cyclobutadiene, followed by cyclopropanation and thermal fragmentation have been shown to be an effective strategy for the preparation of bicyclo[5.3.0]decane ring systems. Herein, we will describe the application of this methodology toward the medium ring containing natural products pleocarpenene and pleocarpenone.

 

Metal-Mediated Reactions and Syntheses
8:00 AM-12:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- C302, Oral

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006