This work describes studies aimed at the synthesis of simple analogs of antibiotic tetracycline(TC) and flavonoid. The synthesis of proposed analogs of tetracycline and flavonide has been accomplished from readily available compounds 9 and 15. The 1,3-cyclohexanedione derivative 9 was transformed to the benzoate derivative 12 followed by base-mediated intramolecular benzoylation to give the bicyclic TC-analog 13. The bicyclic TC-analog 25 and the flavonoid-analogs 26 and 27 have been prepared from the quinol derivative 15.