Kedarcidin Chromophore: Synthesis of Its Proposed Structure and Evidence for a Stereochemical Revision
| Autor: | Andrew G. Myers, and Alan J. Anderson, Feng Ren, Philip C. Hogan |
|---|---|
| Rok vydání: | 2007 |
| Předmět: |
Magnetic Resonance Spectroscopy
Stereochemistry Longest linear sequence Molecular Conformation Stereoisomerism Naphthalenes Biochemistry Mass Spectrometry Article Catalysis Residue (chemistry) Colloid and Surface Chemistry Spectroscopy Fourier Transform Infrared Aza Compounds Antibiotics Antineoplastic Chemistry Enantioselective synthesis Cycloparaffins General Chemistry Nuclear magnetic resonance spectroscopy Chromophore Yield (chemistry) Proton NMR Indicators and Reagents Enediynes |
| Zdroj: | Journal of the American Chemical Society. 129:5381-5383 |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/ja071205b |
| Popis: | A convergent, enantioselective synthesis of the proposed structure of kedarcidin chromophore (1) is described. The route is 24 steps in the longest linear sequence (beginning with the commercial reagent 2,3-O-isopropylidene-d-erythronolactone) with an average yield of 75% per step (overall yield: 0.1%). Our 1H NMR data for 1 do not coincide with the data reported for kedarcidin chromophore. We have re-analyzed the original data and here propose a stereochemical revision at position C10, the site of attachment of the l-mycarose carbohydrate residue to the chromophore core (structure 2). |
| Databáze: | OpenAIRE |
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