Concise, Stereoselective Route to the Four Diastereoisomers of 4-Methylproline

The full stereochemical characterization of 4-methylproline, a rare amino acid found in a number of peptidic secondary metabolites, has often been hindered by long reaction sequences or low stereoselectivity in the synthesis leading to reference samples. The preparation of the four diastereoisomers...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2008-05, Vol.71 (5), p.806-809
Main Authors: Murphy, Annabel C., Mitova, Maya I., Blunt, John W., Munro, Murray H. G.
Format: Article
Language:English
Subjects:
Aliphatic compounds
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Organic chemistry
Preparations and properties
Proline - analogs & derivatives
Proline - chemical synthesis
Proline - chemistry
Stereoisomerism
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Summary:The full stereochemical characterization of 4-methylproline, a rare amino acid found in a number of peptidic secondary metabolites, has often been hindered by long reaction sequences or low stereoselectivity in the synthesis leading to reference samples. The preparation of the four diastereoisomers of 4-methylproline by a concise and stereoselective route is presented and features a six-step route with late-stage stereodivergence, good stereoselectivity for both cis- and trans-series (75% and 88% de, respectively), and good overall yields (cumulative yields of 30–40%). Additional data on the Marfey’s derivatives of the stereoisomers are also presented.
ISSN:0163-3864
1520-6025
DOI:10.1021/np070673w