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Issue 26, 2018
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A synthesis-enabled relative stereochemical assignment of the C1–C28 region of hemicalide

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Abstract

Through synthesising both candidate diastereomers of a model C1–C28 fragment of the potent cytotoxic marine polyketide hemicalide, an assignment of the relative configuration between the C1–C15 and C16–C26 regions has been achieved. By detailed NMR comparisons with the natural product, the relative stereochemistry between these two 1,6-related stereoclusters is elucidated as 13,18-syn rather than the previously proposed 13,18-anti relationship. A flexible and modular strategy using an advanced C1–C28 ketone fragment 22 is outlined to elucidate the remaining stereochemical features and achieve a total synthesis.

Graphical abstract: A synthesis-enabled relative stereochemical assignment of the C1–C28 region of hemicalide

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Publication details

The article was received on 02 Feb 2018, accepted on 16 Feb 2018 and first published on 14 Mar 2018


Article type: Communication
DOI: 10.1039/C8CC00933C
Citation: Chem. Commun., 2018,54, 3247-3250
  • Open access: Creative Commons BY license
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    A synthesis-enabled relative stereochemical assignment of the C1–C28 region of hemicalide

    B. Y. Han, N. Y. S. Lam, C. I. MacGregor, J. M. Goodman and I. Paterson, Chem. Commun., 2018, 54, 3247
    DOI: 10.1039/C8CC00933C

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