Progress towards the total synthesis of Laurenditerpenol, an HIF-1 inhibitor

ORGN 709

Michael E. Jung, jung@chem.ucla.edu and G-Yoon Jamie Im, gyim@chem.ucla.edu. Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, CA 90095-1569
The progress towards the total synthesis of Laurenditerpenol (1), an inhibitor of the hypoxia-inducible factor-1 (HIF-1) in tumor cells, is described. An intermolecular Diels-Alder reaction between maleic anhydride and 2,5-dimethylfuran followed by enantiomeric ring-opening, deoxygenation, and homologation furnishes the hindered bicycle 3. Alkylation, reduction, and lactonization of 3-methyl-2-cyclohexenone furnishes the lactone 2. Regioselective alkylation, hydrolysis, and deoxygenation are expected to yield the title compound. Stereochemistry at C6 and C7 will be determined and compared to the natural product.

 

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

Sci-Mix
8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Division of Organic Chemistry

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