Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 15, Issue 3, Pages 649-661Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6ob02523d
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Funding
- National Natural Science Foundation of China [21472022, 21272041, 21072034]
- China Postdoctoral Science Foundation [KLF301012]
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A diastereoselective approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones 1 (P-1 = TBS, P-2 = H) has been developed through a stereoselective tandem Barbier process of (R, S-RS)-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 alpha-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.
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