Philippe Chemla

Stereoselective synthesis of (+)-hydantocidin

Abstract The naturally occurring spironucleoside (+)-hydantocidin 1 was synthesized from 1,2:3,4-di- O -isopropylidene-D-psicofuranose using a new oxygen-bridged intramolecular Vorbruggen coupling of the N-hydroxyurea 5 in presence of a catalytic amount of trimethylsilyltriflate.

An Enzyme‐Bound Bisubstrate Hybrid Inhibitor of Adenylosuccinate Synthetase

Two relatively weak herbicides, hydantocidin phosphate and hadacidin were linked by a C(3) chain to afford a potent inhibitor (the 2S hybrid is shown) of the enzyme adenylosuccinate synthetase. The crystal structures of the bisubstrate-enzyme complexes were determined.

Synthesis of surrogate structures related to the herbicidal agent hydantocidin

Abstract The synthesis of a spirohydantoin derivative of D-erythrose has been accomplished in the quest to understand the functional requirements for the herbicidal activity of hydantocidin.

Natural products as pesticides: Two examples of stereoselective synthesis†

The strategy and synthetic efforts leading to efficient stereoselective syntheses of thiangazole, a tris-thiazolinyl-oxazole metabolite isolated from Polyangium spp., and of hydantocidin, a spironucleoside metabolite isolated from Streptomyces hygroscopicus, are discussed.