|Abstract with Figure|
University of Wisconsin - River Falls
Subject Listing - Chemistry
Advisor: Dr. Karl Peterson
Friday, Poster Session 5, Presentation Kiosk 23 B, Health & Fitness Center
TOWARD THE SYNTHESIS OF (-)-INCARVILLINE AND (-)-INCARVILLATEINE
Recent investigations into the therapeutic properties of the plant Incarvillea sinensis have revealed the presence of a novel monoterpene alkaloid that was named (-)-incarvillateine. This compound has been found to have antinociceptive activity comparable to that of morphine, but at slightly lower dosage levels. Additionally, (-)-incarvillateine is reported to operate through the adenosyl rather than the opiate receptor mechanism. The first total synthesis of (-)-incarvillateine was reported in 2004. The overall goal of this project was to complete the enantioselective total synthesis of (-)-incarvilline and (-)-incarvillateine by following a significantly shorter synthetic scheme. The synthesis of (-)-incarvillateine was broken down into the separate syntheses of the 2,4-diaryl-1,3-dicarboxylic acid core and the bicyclic aminoalcohol, (-)-incarvilline. The 2,4-diaryl-1,3-dicarboxylic acid core has been successfully synthesized from vanillin in four steps. The key reaction involved a [2+2] photochemical dimerization of the 4-O-tosyl derivative of ferulic acid. A nine step synthesis of (-)-incarvilline has been designed starting with (-)-carvone and including a notable Favorskii rearrangement of the O-protected chlorohydrin derivative of (-)-carvone. The final step of the synthesis assembles (-)-incarvillateine through esterification of (-)-incarvilline with the 2,4-diaryl-1,3-dicarboxylic acid core.
Advisor: Dr. Karl Peterson, Associate Professor, Chemistry, University of Wisconsin - River Falls, River Falls, WI