ChemInform Abstract: Syntheses of Althiomycin Analogues in Relation to Antibacterial Activities.

ChemInform Abstract

Theester (I) is coupled with the pyrrolinone (II) to give (III). Detritylation of (III) followed by reaction with the aminoacetimidate (IV) affords the (R)-thiazolinylcarbonylpyrrolinone (Va). Introduction of the hydroxymethyl group gives (Vb), which un-dergoes deprotection and coupling with the thiazole (VII) by the azide methodusing K₂CO₃ as base to give the (R)-con?gurated epialthiomycin (VI IIa). By thesamc reaction, the (S)-de(hydroxymethyl) analogue (VIIIb) is prepared from theknown key intermediate (Vc). The (Z)-althiomycin (IX) is obtained from the natural(E)-isomer (VIIIc) by isomerization using anhydrous HF.