Jump to main content
Jump to site search

Issue 3, 2017
Previous Article Next Article

An efficient approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones through a stereoselective tandem Barbier process: divergent syntheses of (3R,4S)-statines, (+)-preussin and (−)-hapalosin

Author affiliations

Abstract

A diastereoselective approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones 1 (P1 = TBS, P2 = H) has been developed through a stereoselective tandem Barbier process of (R,SRS)-8 with alkyl and aryl bromide. The stereochemistry at the C-5 stereogenic center of the trans-4-hydroxy-5-substituted 2-pyrrolidinones was solely controlled by α-alkoxy substitution. This effective approach was successfully used to prepare a variety of substituted (3R,4S)-statines 2. In addition, two bioactive natural products of (+)-preussin 4 and hapalosin 5 were effectively synthesized through this stereoselective tandem Barbier process.

Graphical abstract: An efficient approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones through a stereoselective tandem Barbier process: divergent syntheses of (3R,4S)-statines, (+)-preussin and (−)-hapalosin

Back to tab navigation

Supplementary files

Publication details

The article was received on 18 Nov 2016, accepted on 08 Dec 2016 and first published on 08 Dec 2016


Article type: Paper
DOI: 10.1039/C6OB02523D
Citation: Org. Biomol. Chem., 2017,15, 649-661
  •   Request permissions

    An efficient approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones through a stereoselective tandem Barbier process: divergent syntheses of (3R,4S)-statines, (+)-preussin and (−)-hapalosin

    C. Si, L. Shao, Z. Mao, W. Zhou and B. Wei, Org. Biomol. Chem., 2017, 15, 649
    DOI: 10.1039/C6OB02523D

Search articles by author

Spotlight

Advertisements