Total synthesis of montanin A

ORGN 166

Hsing-Jang Liu, hjliu@mx.nthu.edu.tw1, Jia-Liang Zhu, jlzhu@mail.ndhu.edu.tw2, I-Chia Chen, msjackie@ms15.hinet.net3, and Yen-Ku Wu, wuyenku@yahoo.com.tw1. (1) Department of Chemistry, National Tsing Hua University, Hsinchu 300, Taiwan, (2) Department of Chemistry, National Dong Hwa University, Hualien 974, Taiwan, (3) Institute of Chemistry, Academia Sinica, Taipei 115, Taiwan
A large number of 19-norclerodane 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. Montanin A (1) is a representative member of this family. This compound was first isolated from Bulgarian Teucrium montanum L by Malakov in 1978. In addition to the presence of four stereogenic centers, the salient structural features of this compound include a decalin core together with a bridged furan ring and a spiro gamma-lactone with a 3-furyl group. The total synthesis of montanin A 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.

 

Asymmetric Reactions and Syntheses, Physical Organic Chemistry, Combinatorial Chemistry, Total Synthesis
8:00 PM-10:00 PM, Sunday, 26 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Division of Organic Chemistry

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