Sequential treatment of 2,3-dichloropropene with magnesium and n-BuLi generates the operational equivalent of 1,3-dilithiopropyne, which upon treatment with aldehydes or ketones, produces the corresponding alkoxy lithium acetylide intermediates. Reaction of this alkoxide with tosyl chloride, and t-BuLi produces 1-substituted, or 1,1-disubstituted 1,3-enynes in a one-pot reaction. When this lithium acetylide intermediates, obtained by this procedure, were used to perform palladium-catalyzed cross-coupling reactions, followed by addition of thionyl chloride and pyridine, 1,4-disubstituted or 1,1,4-trisubstituted 1,3-enynes were obtained in a one-pot protocol.

Natural product jacaranone, 1, and three analog derivatives were synthesized and their apoptotic and necrotic activity against four cancer cell lines was tested. One of these derivatives 7, was more active than the natural product, and exhibited an important necrotic effect against three of the cell lines tested (ovarian carcinoma, liver cancer and breast cancer cells). Derivative 6 was more active than the natural product, and showed a significant apoptotic activity against breast cancer and ovarian carcinoma cells. Some derivatives analyzed in this study showed promising anti-tumor results, nevertheless, further studies have to be done in order to determine their in vivo activity, their mechanism as well as their safety and stability.