A Short and Elegant Synthesis of (±)‐Streptopyrrolidine. (4th April 2013)

• Record Type: Journal Article
• Authors: Shaameri, Zurina; Ali, Sharifah Hidayah Sharif; Mohamat, Mohd Fazli; Yamin, Bohari M.; Hamzah, Ahmad Sazali
• Is Part Of: Journal of heterocyclic chemistry. Volume 50:Number 2(2013:Mar.)
• Page Start: 320
• Page End: 325
• Publication Date: 2013-04-04
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.1078
• Languages: English
• ISSNs: 0022-152X

Abstract

<abstract abstract-type="main" xml:lang="en" id="jhet1078-abs-0001"> <title> <x xml:space="preserve">Abstract</x> </title> <p id="jhet1078-para-0001">A brief and efficient approach for the synthesis of (±)‐5‐benzyl‐4‐hydroxy‐2‐pyrrolidine (<xref ref-type="link" rid="jhet1078-fig-0005">1</xref>) from phenylalanine racemate is described. The key step is the stereocontrolled reduction of the keto functionality of benzylated pyrrolidinone intermediate (<xref ref-type="link" rid="jhet1078-fig-0005">1</xref>) <italic>via</italic> sodium borohydride in carboxylic acid medium furnishing both (<italic>R</italic>, <italic>R</italic>)‐ and (<italic>S</italic>, <italic>S</italic>)‐configured diastereomers. The natural (<italic>R</italic>, <italic>R</italic>) enantiomer (<xref ref-type="link" rid="jhet1078-fig-0001">1</xref>), however, crystallized out from its racemic mixture. Structure of <xref ref-type="link" rid="jhet1078-fig-0001">1</xref> was confirmed by NMR, IR, elemental analyzer, and single crystal X‐ray crystallographic techniques.</p> </abstract>