PROGRESS TOWARDS THE SYNTHESIS OF TYPE B POLYCYCLIC POLYPRENYLATED ACYLPHLOROGLUCINOL 7-epi-CLUSIANONE

Author

Pushpa Suresh Jayasekara Mudiyanselage, University of KentuckyFollow

Date Available

12-14-2011

Year of Publication

2010

Degree Name

Doctor of Philosophy (PhD)

Document Type

Dissertation

College

Arts and Sciences

Department

Chemistry

First Advisor

Dr. R.B. Grossman

Abstract

Plants of the family Guttiferae produce polycyclic polyprenylated acylphloroglucinols (PPAPs), which have interesting biological activities 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. 7-epi-Clusianone, a type B PPAP with C-7 endo stereochemistry, is being approached by establishing the cis relationship with C(4) allyl group and C(2) methyl ester in the early stage of the synthesis. Then C(2) methyl ester is converted to alkyne aldehyde and syn reduction followed by intramolecular aldol reaction to give bicyclo[3.3.1]nonane structure with C(7) endo stereo chemistry.

Recommended Citation

Mudiyanselage, Pushpa Suresh Jayasekara, "PROGRESS TOWARDS THE SYNTHESIS OF TYPE B POLYCYCLIC POLYPRENYLATED ACYLPHLOROGLUCINOL 7-epi-CLUSIANONE" (2010). University of Kentucky Doctoral Dissertations. 758.
https://uknowledge.uky.edu/gradschool_diss/758