Synthetic approach to Type B polycyclic polyprenylated acylphloroglucinols (PPAPs): Total synthesis toward Xanthochymol and 7-epi-Clusianone

ORGN 464

M. P. Suresh Jayasekara, sjayasekara@uky.edu and Robert B. Grossman, robert.grossman@uky.edu. Department of Chemistry, University of Kentucky, 125 Chemistry-Physics Building, Lexington, KY 40506
Plants of the family Guttiferae produce polycyclic polyprenylated acylphloroglucinols (PPAPs), which have interesting biological including anticancer and antibacterial properties. The main structural features of PPAPs comprise of bicyclo[3.3.1]nonane-2,4,9-triketone with one acyl group together with prenyl, geranyl, or other C10H17 groups. Few research groups have published synthetic strategies for the PPAPs with the C-7 prenyl group in the endo orientation. The synthesis of type B PPAP natural products, including xanthochymol and 7-epi-clusianone, is being approached by syn reduction of an alkyne with Co2(CO)8 and Et3SiH and an intramolecular aldol reaction.

 

Total Synthesis of Complex Molecules
8:00 AM-12:00 PM, Wednesday, April 9, 2008 Morial Convention Center -- Rm. R05, Oral

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008