SYNTHESIS OF α, ω-DIKETODIESTERS FROM BETULIN

A new synthesis of 3-oxo-28-hydroxylup-20(29)-ene from the available natural triterpenoid betulin was developed. alpha,omega-Diketodiesters were prepared for the first time by different methods from 3-oxo-28-hydmxylup-20(29)-ene and a series of natural dicarboxylic acids. Steglich reaction conditions gave the highest yields. One of the synthesized alpha, omega-diketodiesters was moderately active in vitro against A-549 lung carcinoma.

Automated summary

A new synthesis method was developed to produce 3-oxo-28-hydroxylup-20(29)-ene from the natural triterpenoid betulin. Alpha, omega-diketodiesters were successfully prepared for the first time by different methods, with the highest yields obtained under Steglich reaction conditions. One of the synthesized alpha, omega-diketodiesters exhibited moderate in vitro activity against A-549 lung carcinoma cells.