Abstract
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).
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Antibiotics, Antineoplastic / chemical synthesis
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Antibiotics, Antineoplastic / chemistry*
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Aza Compounds / chemistry
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Cycloparaffins / chemical synthesis
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Cycloparaffins / chemistry*
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Enediynes / chemical synthesis
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Enediynes / chemistry*
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Indicators and Reagents
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Magnetic Resonance Spectroscopy
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Mass Spectrometry
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Molecular Conformation
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Naphthalenes / chemical synthesis
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Naphthalenes / chemistry*
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Spectroscopy, Fourier Transform Infrared
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Stereoisomerism
Substances
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Antibiotics, Antineoplastic
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Aza Compounds
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Cycloparaffins
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Enediynes
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Indicators and Reagents
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Naphthalenes
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kedarcidin chromophore