Total synthesis of Gomisin O

ORGN 191

Soumya Mitra, smitra@chemistry.ohio-state.edu, Srinivas Reddy Gurrala, and Robert S. Coleman. Department of Chemistry, The Ohio State University, 100 W 18th Avenue, Newman Wolfrom Laboratory of Chemistry, Columbus, OH 43210-1185
Gomisins are one of the pharmacologically important components isolated from the oriental medicine “gomisi”, the fruits of Schisandra chinensis. Members of the Gomisin family possess anti-HIV, antineoplastic, CNS depressant, analgesic, antitussive and antihepatotoxic properties. Total syntheses of the dibenzocyclooctadiene lignans Gomisin O and Epigomisin O are reported. The synthesis was based on an atropdiastereoselective copper-promoted intramolecular oxidative Lipshutz biaryl cross-coupling reaction, a diastereoselective in situ hydroboration /beta-alkyl Suzuki-Miyaura cross coupling reaction sequence, and an Indium mediated tiglylation of an aryl aldehyde precursor. Details of the synthesis and recent advances in this area will be presented.

 

New Reactions and Methodology, Materials, Total Synthesis, Process R&D
8:00 PM-10:00 PM, Sunday, 28 August 2005 Washington DC Convention Center -- Hall A, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005