Synthetic studies toward the Lycopodium alkaloid nankakurine A

ORGN 750

Ellen D. Beaulieu, ledowns@berkeley.edu, Juliette R. Petersen, and Dirk Trauner, trauner@berkeley.edu. Department of Chemistry, University of California, Berkeley, Room B84 Hildebrand Hall, University of California, Berkeley, CA 94720
Nankakurine A is a tetracyclic alkaloid isolated from the club moss Lycopodium hamiltonii whose structure was elucidated in 2004. The natural product features a 3-aza-bicyclo[3.3.1]nonane ring system fused to a piperidine ring through a spiro center. Our synthesis utilizes a formal aza-ene cyclization to rapidly access the tricyclic core. A systematic investigation of hydroamination methods to construct the spiro piperidine ring is also detailed.

 

Total Synthesis, Materials, Molecular Recognition, Process R&D, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 13 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006