A convergent, enantioselective synthesis of the proposed structure of kedarcidin chromophore () is described. The route is 24 steps in the longest linear sequence (beginning with the commercial reagent 2,3--isopropylidene-d-erythronolactone) with an average yield of 75% per step (overall yield: 0.1%). Our H NMR data for 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 ).
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| http://dx.doi.org/10.1021/ja071205b | DOI Listing |
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A convergent total synthesis of the kedarcidin chromophore: 20-years in the making.
J Antibiot (Tokyo)
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Department of Chemistry, Graduate School of Science, Tohoku University, Aza Aramaki, Aoba-ku, Sendai, 980-8578, Japan.
The kedarcidin chromophore is a formidible target for total synthesis. Herein, we describe a viable synthesis of this highly unstable natural product. This entailed the early introduction and gram-scale synthesis of 2-deoxysugar conjugates of both L-mycarose and L-kedarosamine.
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Proc Natl Acad Sci U S A
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Department of Chemistry, The Scripps Research Institute, Jupiter, FL 33458, USA.
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Department of Chemistry, The Scripps Research Institute, Jupiter, Florida 33458, USA.
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Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
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