I. "One-pot" cyclopentenone synthesis via the acetonyl synthetic equivalent 3-chloro-2-diethylphosphoryloxy-1-propene ; II. Isolation and characterization of cycloseychellene from patchouli oil

A new acetonyl synthetic equivalent 3-chloro-2-diethyl- phosphoryloxy-l-propene is reported. This reagent can undergo alkylation, then hydrolysis under mild acidic conditions to afford an acetonyl unit. More interestingly, utilization of this reagent permits a convenient "one-pot" conversion of a ketone to a cyclopentenone. Short syntheses of various cyclopentenones via this route, alkylation of an enolate anion with 3-chloro-2-diethyl- phosphoryloxy-l-propene followed by in situ base hydrolysis, is described. Applications of this methodology to new syntheses of cis-jasmone, and methylenomycin B are also described. The isolation of the sesquiterpene cycloseychellene from West Indian Patchouli Oil is described.