A Search For Phenolic Protection in Virginiamycin S

Abstract

In order to be able to mask the hydroxyl grouping of the pipecolic ac,id,residue in Virginiamycin during alkaline (NaOH) and acidic Ffa) break-down rocedures and to use peptidic fragments coming thereof for further reconstitution by classical peptide sy nttesis procedures, we have investigated several, candidates for protection/deprotection. Thus the phenacyl derivatives (4 & the allyloycarbonyl derivative (E), the trichloroethyloxycarbonyl derivatives (8 & and the 2,4-dinitro%enyl derivative (a) have been prepared.Among these none were stable in aqueous9basic conditions. The Alloc-6) the Troc (8) and Dnp-derivative (m) may have some applications under acidic conditions.