title: Stereoselective synthesis of four possible isomers of streptopyrrolidine.
abstract: The synthesis of (4R,5R)-streptopyrrolidine (1), (4S,5R)-streptopyrrolidine (2) (4R,5S)-streptopyrrolidine (3) and (4S,5S)-streptopyrrolidine (4) have been achieved in a concise and highly efficient manner via a highly stereoselective aldol type reaction with the trimethylsilyl enolate of ethyl acetate and Lewis acid mediated lactamization as the key reactions in ≈42% yield over six steps starting from D-phenylalanine and L-phenylalanine, respectively. The absolute configuration of the natural product was shown to be (4S,5S) by comparing its spectral and analytical data with the reported values.
authors.affiliation: Division of Organic Chemistry-I, Indian Institute of Chemical Technology (CSIR), Hyderabad-500607, India, Tel/
authors.forename: Debendra K
authors.initials: DK
authors.lastname: Mohapatra
authors.forename: Barla
authors.initials: B
authors.lastname: Thirupathi
authors.forename: Pragna P
authors.initials: PP
authors.lastname: Das
authors.forename: Jhillu S
authors.initials: JS
authors.lastname: Yadav