Total synthesis of teuscorolide

ORGN 722

Hsing-Jang Liu, hjliu@mx.nthu.edu.tw1, I-Chia Chen, msjackie@ms15.hinet.net2, Yen-Ku Wu, wuyenku@yahoo.com.tw1, and Jia-Liang Zhu, jlzhu@mail.ndhu.edu.tw3. (1) Department of Chemistry, National Tsing Hua University, Hsinchu 300, Taiwan, (2) Institute of Chemistry, Academia Sinica, Taipei 115, Taiwan, (3) Department of Chemistry, National Dong Hwa University, Hualien 974, Taiwan
A large number of 19-nor-clerodane diterpenoids have been isolated in the past decades. These compounds have attracted extensive interest owing to their biological activity, especially as insect antifeedants and as antitumor, antimicrobial, and antifungal agents. Teuscorolide (1) is a representative member of this family. This compound was first isolated from the aerial part of Teucrium scorodonia L. by Rodriguez in 1982. In addition to the presence of four stereogenic centers, the salient structural features of this compound include a decalin core together with a bridged γ-lactone and a spiro γ-lactone. The total synthesis of teuscorolide has been achieved in our laboratory via an intermolecular Diels-Alder cycloaddition between dienophile 2 and diene 3. Details of the synthesis will be described.

 

 

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