A synthesis-enabled relative stereochemical assignment of the C1-C28 region of hemicalide.
Chemical communications (Cambridge, England)
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Han, B. Y., Lam, N., MacGregor, C. I., Goodman, J., & Paterson, I. (2018). A synthesis-enabled relative stereochemical assignment of the C1-C28 region of hemicalide.. Chemical communications (Cambridge, England), 54 (26), 3247-3250. https://doi.org/10.1039/c8cc00933c
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 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.
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External DOI: https://doi.org/10.1039/c8cc00933c
This record's URL: https://www.repository.cam.ac.uk/handle/1810/275443
Attribution 4.0 International
Licence URL: http://creativecommons.org/licenses/by/4.0/
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