Synthesis of Phosphonomethyl Tetrahydrofurans via the Mori-Tamaru Reaction of Phosphonodienes.

Nickel-catalyzed reductive addition of phosphonodienes to aldehydes (the Mori-Tamaru reaction) gives hydroxy vinyl phosphonates in good yields with excellent control of the relative stereochemistry. Base-induced cyclization of the vinyl phosphonates yields phosphonomethyl-substituted tetrahydrofurans. Inversion of the hydroxyl stereochemistry by Mitsunobu reaction and then cyclization yields a different set of phosphonomethyl-substituted tetrahydrofuran diastereoisomers.

Cyclipostins and Cyclophostin Analogues as Multitarget Inhibitors That Impair Growth of .

Twelve new Cyclophostin and Cyclipostins analogues () were synthesized, thus extending our series to 38 . Their antibacterial activities were evaluated against four pathogenic mycobacteria (, , BCG, and ) and two Gram negative bacteria. The displayed very low toxicity toward host cells and were only active against mycobacteria.

Relay cross metathesis reactions of vinylphosphonates.

Dimethyl (β-substituted) vinylphosphonates do not readily undergo cross metathesis reactions with Grubbs catalyst and terminal alkenes. However, the corresponding mono- or diallyl vinylphosphonate esters undergo facile cross metathesis reactions. The improved reactivity is attributed to a relay step in the cross metathesis reaction mechanism.