Synthesis and bioactivity of new analogue of Bicyclic 1-Azafagomine

Abstract

New (S)-(1,2,3,6-tetrahydropyridazin-3-yl)methanol was synthesized by Lewis acid catalyzed and self-assembled Diels-Alder (LACASA-DA) cycloaddition reaction using (S)-BINOL as a chiral inductor. The N-2 pyridazine position was protected, the hydroxyl group was carbonylated to form the new bicyclic structure. The protective group was removed and the double bond was dihydroxylated leading to the target compound. Removal of the protective group was performed using a newly found ecofriendly catalyst for N-Boc deprotection. The final iminosugar derivative 7 and all newly synthesized intermediates, were investigated against S. aureus and E. coli bacteria and were found to show promising activity against both gram-positive and gram-negative bacteria.