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Solid-Phase Synthesis and Configurational Reassigment of Callipeltin E. Implications for the Structures of Callipeltins A and B

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    Solid-Phase Synthesis and Configurational Reassigment of Callipeltin E. Implications for the Structures of Callipeltins A and B
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    Department of Chemistry and Cancer Center, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2006, 71, 17, 6351–6356
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    https://doi.org/10.1021/jo060351h
    Published July 21, 2006
    Copyright © 2006 American Chemical Society
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    Abstract

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    Two possible isomers of the natural product callipeltin E (1, 5) were synthesized by using an Fmoc-based solid-phase strategy in 7 steps, in 20% and 26% overall yields, respectively. The 1H NMR spectrum of synthetic 5 correlated closely with that of the natural product, whereas that of 1 did not, providing confirmation of the configurational reassignment of the N-terminal residue of callipeltin E as d-allothreonine. This result strongly implies that the corresponding residue in the closely related cyclic depsipeptides callipeltins A and B should also be considered a d-allothreonine residue.

    Copyright © 2006 American Chemical Society

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    Cited By

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2006, 71, 17, 6351–6356
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo060351h
    Published July 21, 2006
    Copyright © 2006 American Chemical Society
    Request reuse permissions

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