Synthesis and antifungal activity of C-21 steroids with an aromatic D ring

Six analogues of salpichrolides with a simplified side chain (6–11) were synthesized using a new methodology to obtain steroids with an aromatic D-ring. The key step was the elimination of HBr in a vicinal dibromo D-homosteroid by treatment with 1,4-diazabicyclo[2.2.2]octane (DABCO). All new compounds were completely characterized by 2D NMR techniques and tested on two fungal pathogenic species, Fusarium virguliforme and Fusarium solani.

► A simple methodology for the preparation of steroids with an aromatic D ring was developed. ► Six analogues of salpichrolides with an aromatic D ring and a simplified side chain were synthesized. ► The antifungal activity was evaluated on two fungal pathogenic species: Fusarium virguliforme and Fusarium solani. ► Two analogues had activity comparable to the natural salpichrolides.