N,N-Acetals as N-Acyliminium Ion Precursors: Synthesis and Absolute Stereochemistry of Epiquinamide

descriptionPublicationkeyboard_double_arrow_right Article 15 Aug 2008 Netherlands English Publisher:American Chemical Society (ACS)Journal:Organic Letters, volume 10, pages 4,001-4,003 (issn: 1523-7060, eissn: 1523-7052,

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Authors: Wijdeven, M.A.; Wijtmans, R.; Berg, R.J.F. van den; Noorduin, W.L.; Schoemaker, H. E.; Sonke, T.; Delft, F.L. van; +5 Authors

doi: 10.1021/ol801490m

pmid: 18702495

handle: https://repository.ubn.ru.nl/handle/2066/72776 , 2066/72776

N,N-Acetals as N-Acyliminium Ion Precursors: Synthesis and Absolute Stereochemistry of Epiquinamide

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Abstract

A stereoselective synthesis of (+)-epiquinamide is presented in combination with determination of the absolute configuration of the natural product. Key steps in the sequence involved chemoenzymatic formation of an enantiomerically pure cyanohydrin, reductive cyclization to the corresponding cyclic N,N-acetal, and subsequent conversion into a suitable N-acyliminium ion precursor to enable construction of the second ring.

Country

Netherlands

Related Organizations

Radboud University Nijmegen
Netherlands
National Institute of Health
Pakistan
National Institutes of Health
United States
Indiana State University
United States
National Institute of Diabetes and Digestive and Kidney Diseases
United States

Keywords

Biological Products, Acetals, Cations, Animals, Stereoisomerism, Solid State Chemistry, Synthetic Organic Chemistry, Imines, Anura, Quinolizines, Substrate Specificity

14 Research products, page 1 of 2

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