Bakers' yeast reductions of β-oxopyrrolidinecarboxylates: synthesis of (+)-cis-(2R,3S)-3-hydroxyproline and (–)-(1S,5S)-Geissman–Waiss lactone, a useful precursor to pyrrolizidine alkaloids
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 12,p. 1313-1317
- https://doi.org/10.1039/p19930001313
Abstract
Bakers' yeast reduction of the β-oxo proline derivative 5 leads to the cis-hydroxy ester 6 and thence to (+)-cis-(2R, 3S)-3-hydroxyproline 7, with > 90% enantiomeric enrichment. Subsequent one-carbon homologation leads to the (–)-Geissman–Waiss lactone 8, a useful precursor of pyrrolizidine alkaloids.Keywords
This publication has 36 references indexed in Scilit:
- Total synthesis of (–)-α-kainic acidJournal of the Chemical Society, Perkin Transactions 1, 1992
- Baker's Yeast as a Reagent in Organic SynthesisSynthesis, 1990
- Total synthesis of 3(S)-carboxy-4(S)-hydroxy-2,3,4,5-tetrahydropyridazine, an unusual amino acid constituent of luzopeptin AThe Journal of Organic Chemistry, 1989
- Recent advances in the use of enzyme-catalysed reactions in organic research: the synthesis of biologically active natural products and analoguesNatural Product Reports, 1986
- Synthese vonrac-DetoxininEuropean Journal of Organic Chemistry, 1983
- Synthesis of 6S, 7S-anhydro-serricornine.Tetrahedron Letters, 1982
- Asymmetric reductinon of carbonyl compounds by yeast. II. Preparation of optically active α- and β-hydroxy carboxylic acid derivativesAustralian Journal of Chemistry, 1976
- The Synthesis of cis- and trans-3-Hydroxy-L-proline, Two New Amino Acids from the Antibiotic TelomycinJournal of the American Chemical Society, 1963
- One-Step Synthesis and Enzymatic Resolution of cis- and trans-3-HydroxyprolineJournal of the American Chemical Society, 1963
- Isolation, Configuration, and Synthesis of Natural cis- and trans-3-HydroxyprolinesJournal of the American Chemical Society, 1963