An enantioselective synthesis of the C3-C21 segment of the macrolide immunosuppressive agent FR252921.
An enantioselective synthesis of the C3-C21 segment of the novel immunosuppressant FR252921 is described. The C12 and C13 stereogenic centers were constructed by a non-aldol process utilizing optically active 4-phenylbutyrolactone. The C18 stereogenic center was installed using Braun's highly diastereoselective acetate aldol reaction. Other key steps involved Curtius rearrangement and Horner-Wadsworth-Emmons olefination reactions.
Department of Chemistry and Department of Medicinal Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, United States.
Arun K
AK
Ghosh
Department of Chemistry and Department of Medicinal Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, United States.
Samuel
S
Rodriguez
FR252921; Macrolide; Synthesis; aldol reaction; asymmetric; asymmetric reduction; immunosuppressive